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Mini-Reviews in Organic Chemistry

Author(s): Carlos Magno Rocha Ribeiro*, Thiago Silva Galvão de Souza, Karinne Canevalli de Almeida, Karen Danielle Borba Dutra and Alessandra Leda Valverde

DOI: 10.2174/1570193X16666190405102658

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Heliannuol: Distribution, Biological Activities, 1H and 13C-NMR Spectral Data

Page: [309 - 322] Pages: 14

  • * (Excluding Mailing and Handling)

Abstract

Heliannuols are an important class of compounds isolated from Helianthus annuus, a common sunflower, with allelopathic properties. Interestingly, two of these fourteen compounds have been isolated from a gorgonian, Pseudopterogorgia rigida. This review compiles data on the isolation and biological activity of heliannuols described in the literature and briefly reports the papers describing their syntheses. This review could stimulate research into other natural species and syntheses. Further, it describes the 1H and 13C-NMR spectral data described in the literature for the 14 heliannuols already isolated and correlates them with their respective structures. Therefore, we believe that these searchable data enable a rapid identification in routine analysis of the crude extracts of sunflowers or gorgonians.

Keywords: 1H and 13C-NMR spectral data, biological activities, distribution, gorgonian, heliannuols, sunflower.

Graphical Abstract

[1]
Karamac, M.; Kosinska, A.; Estrella, I.; Hernández, T.; Dueñas, M. Antioxidant activity of phenolic compounds identified in sunflower seeds. Eur. Food Res. Technol., 2012, 235, 221-230.
[http://dx.doi.org/10.1007/s00217-012-1751-6]
[2]
Dwivedi, A.; Sharma, G.N. A review on heliotropism: Helianthus annuus L. J. Phytopharmacol, 2014, 3, 149-155.
[3]
Ibrahim, T.A.; Ajongbolo, K.F.; Aladekoyi, G. Phytochemical screening and antimicrobial activity of crude extracts of Basella alba and Helianthus annuus on selected food pathogens. Res. Rev. J. Microbiol. Biotechnol., 2014, 3, 27-31.
[4]
Dwivedi, A.; Sharma, G.N.; Kaushik, A.Y. Evaluation of Helianthus annuus L. leaves extract for the antidiarrheal and antihistaminic activity. Int. J. Res. Ayurveda Pharm., 2015, 6, 118-123.
[http://dx.doi.org/10.7897/2277-4343.06125]
[5]
Miraj, S. Helianthus annuus: A systematic review of pharmacological activity. Pharma Chem., 2016, 8, 73-76.
[6]
Mayer, A.M.S.; Rodríguez, A.D.; Taglialatela-Scafati, O.; Fusetani, N. Marine pharmacology in 2009-2011: marine compounds with antibacterial, antidiabetic, antifungal, anti-inflammatory, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous systems, and other miscellaneous mechanisms of action. Mar. Drugs, 2013, 11(7), 2510-2573.
[http://dx.doi.org/10.3390/md11072510] [PMID: 23880931]
[7]
González, Y.; Torres-Mendoza, D.; Jones, G.E.; Fernandez, P.L. Marine diterpenoids as potential anti-inflammatory agents. Eur. Food Res. Technol.;, 2015, 235, 221-230.
[http://dx.doi.org/10.1155/2015/263543]
[8]
Cantamutto, M.; Poverene, M. Genetically modified sunflower release: Opportunities and risks. Field Crops Res., 2007, 101, 133-144.
[http://dx.doi.org/10.1016/j.fcr.2006.11.007]
[9]
Zanetti, F.; Monti, A.; Berti, M.T. Challenges and opportunities for new industrial oilseed crops in EU-27: A review. Ind. Crops Prod., 2013, 50, 580-595.
[http://dx.doi.org/10.1016/j.indcrop.2013.08.030]
[10]
Prats, E.; Bazzalo, M.E.; León, A.; Jorrín, J.V. Fungitoxic effect of scopolin and related coumarins on Sclerotinia sclerotiorum. A way to overcome sunflower head rot. Euphytica, 2006, 147, 451-460.
[http://dx.doi.org/10.1007/s10681-005-9045-8]
[11]
Kamal, J. Quantification of alkaloids, phenols and flavonoids in sunflower (Helianthus annuus L.). Afr. J. Biotechnol., 2011, 10, 3149-3151.
[http://dx.doi.org/10.5897/AJB09.1270]
[12]
El Marsni, Z.; Torres, A.; Varela, R.M.; Molinillo, J.M.G.; Casas, L.; Mantell, C.; Martinez de la Ossa, E.J.; Macías, F.A. Isolation of bioactive compounds from sunflower leaves (Helianthus annuus L) extracted with supercritical carbon dioxide. J. Agric. Food Chem., 2015, 63(28), 6410-6421.
[http://dx.doi.org/10.1021/acs.jafc.5b02261] [PMID: 26151222]
[13]
Torres, A.; Molinillo, J.M.G.; Varela, R.M.; Casas, L.; Mantell, C.; Martínez de la Ossa, E.J.; Macías, F.A. Helikaurolides A-D with a diterpene-sesquiterpene skeleton from supercritical fluid extracts of Helianthus annuus L. var. Arianna. Org. Lett., 2015, 17(19), 4730-4733.
[http://dx.doi.org/10.1021/acs.orglett.5b02221] [PMID: 26368065]
[14]
Harvell, C.D.; Fenical, W.; Greenel, C.H. Chemical and structural defenses of Caribbean gorgonians (Pseudopterogorgia spp.). I. Development of an in situ feeding assay. Mar. Ecol. Prog. Ser., 1988, 49, 287-294.
[http://dx.doi.org/10.3354/meps049287]
[15]
Maia, L.F.; Epifanio, R.A.; Fenical, W. New cytotoxic sterol glycosides from the octocoral Carijoa (Telesto) riisei. J. Nat. Prod., 2000, 63(10), 1427-1430.
[http://dx.doi.org/10.1021/np9906323] [PMID: 11076570]
[16]
McEnroe, F.J.; Fenical, W. Structures and synthesis of some new antibacterial sesquiterpenoids from the gorgonian coral Pseudopterogorgia rigida. Tetrahedron, 1978, 34, 1661-1164.
[http://dx.doi.org/10.1016/0040-4020(78)80198-7]
[17]
Abreu, P.A.; Wilke, D.V.; Araujo, A.J.; Marinho-Filho, J.D.B.; Ferreira, E.G.; Ribeiro, C.M.R.; Pinheiro, L.S.; Amorim, J.W.; Valverde, A.L.; Epifanio, R.A.; Costa-Lotufo, L.V.; Jumenez, P.C. Perezone, from gorgonian Pseudopterogorgia rigida, induces oxidative stress in human leukemia cells. Braz. J. Pharmacog., 2015, 25, 634-640.
[http://dx.doi.org/10.1016/j.bjp.2015.07.020]
[18]
Georgantea, P.; Ioannou, E.; Evain-Bana, E.; Bagrel, D.; Martinet, N.; Vagias, C.; Roussis, V. Sesquiterpenes with inhibitory activity against CDC25 phosphatases from the soft coral Pseudopterogorgia rigida. Tetrahedron, 2016, 72, 3262-3269.
[http://dx.doi.org/10.1016/j.tet.2016.04.059]
[19]
Price, A.J.; Kelton, J.A. Herbicides - Current Research and Case Studies in Use; InTech: New York, 2013.
[http://dx.doi.org/10.5772/56743]
[20]
Kalyar, T. Rauf. S.; Da Silva, J.A.T.; Shahzad, M. Handling sunflower (Helianthus annuus L.) population under heat stress. Arch. Agron. Soil Sci., 2014, 60, 655-672.
[http://dx.doi.org/10.1080/03650340.2013.799276]
[21]
Nikneshan, P.; Karimmojeni, H.; Moghanibashi, M.; Hosseini, N.S. Allelopathic potential of sunflower on weed management in safflower and wheat. Aust. J. Crop Sci., 2011, 5, 1434-1440.
[22]
Macías, F.A.; Oliveros-Bastidas, A.; Marín, D.; Carrera, C.; Chinchilla, N.; Molinillo, J.M.G. Plant biocommunicators: Their phytotoxicity, degradation studies and potential use as herbicide models. Phytochem. Rev., 2008, 7, 179-194.
[http://dx.doi.org/10.1007/s11101-007-9062-4]
[23]
Macías, F.A.; Galindo, J.C.G.; Molinillo, J.M.G.; Cutler, H.G. Allelopathy: Chemistry and Mode of Action of Allelochemicals; CRC Press: Florida, 2004.
[24]
Kamei, T.; Morimoto, S.; Shishido, K. Synthetic studies on heliannuol sesquiterpenoids with allelopathic activity. Yuki Gosei Kagaku Kyokaishi, 2006, 64, 1021-1031.
[http://dx.doi.org/10.5059/yukigoseikyokaishi.64.1021]
[25]
Shishido, K. Stereocontrolled total synthesis of natural products with characteristic molecular structures and biological activities. Chem. Pharm. Bull. (Tokyo), 2013, 61(8), 781-798.
[http://dx.doi.org/10.1248/cpb.c13-00417] [PMID: 23902860]
[26]
Chen, K.; Li, Y.; Du, Z.; Tao, Z. Total syntheses of heliannuols: An overview. Synth. Commun., 2015, 45, 673-701.
[http://dx.doi.org/10.1080/00397911.2014.979948]
[27]
Sarkar, D.; Ghosh, M.K. Story of helianane and heliannuols - unique structurally diverse benzoxacycles, interesting intrigues and structural anomaly. Curr. Org. Chem., 2018, 22, 18-56.
[http://dx.doi.org/10.2174/1385272822666171222150107]
[28]
Valverde, A.L.; Cardoso, G.L.C.; Pereira, N.A.; Silva, A.J.R.; Kuster, R.M. Analgesic and antiinflammatory activities of vernonioside B2 from Vernonia condensata. Phytother. Res., 2001, 15(3), 263-264.
[http://dx.doi.org/10.1002/ptr.733] [PMID: 11351366]
[29]
Ferraz, H.M.C.; Grazini, M.V.A.; Ribeiro, C.M.R.; Brocksom, U.; Brocksom, T.J. A short route to (-)-mintlactone by thallium(III)-mediated cyclization of (-)-isopulegol. J. Org. Chem., 2000, 65(8), 2606-2607.
[http://dx.doi.org/10.1021/jo991802j] [PMID: 10789485]
[30]
Ribeiro, C.M.R.; Souza, P.P.; Ferreira, L.L.D.M.; Pereira, S.L.; Martins, I.S.; Epifanio, R.A.; Costa-Lotufo, L.V.; Jimenez, P.C.; Pessoa, C.; Moraes, M.O. Natural furano naphtoquinones from lapachol: Hydroxyiso-β-lapachone, stenocarpoquinone-B and avicequinone-C. Lett. Org. Chem., 2011, 8, 347-351.
[http://dx.doi.org/10.2174/157017811795685063]
[31]
Ribeiro, C.M.R.; Souza, P.P.; Ferreira, L.L.D.M.; Pinto, L.A.; Almeida, L.S.; Jesus, J.G. Cyclization of lapachol induced by thallium salts. Quim. Nova, 2008, 31, 759-762.
[http://dx.doi.org/10.1590/S0100-40422008000400009]
[32]
Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G.; Fronczek, F.R. Novel sesquiterpene from bioactive fractions of cultivar sunflowers. Tetrahedron Lett., 1993, 34, 1999-2002.
[http://dx.doi.org/10.1016/S0040-4039(00)91986-5]
[33]
Macías, F.A.; Molinillo, J.M.G.; Varela, R.M.; Torres, A.; Fronczek, F.R. Structural elucidation and chemistry of a novel family of bioactive sesquiterpenes: Heliannuols. J. Org. Chem., 1994, 59, 8261-8266.
[http://dx.doi.org/10.1021/jo00105a052]
[34]
Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Heliannuol E. A novel bioactive sesquiterpene of the heliannane family. Tetrahedron Lett., 1999, 40, 4725-4728.
[http://dx.doi.org/10.1016/S0040-4039(99)00833-3]
[35]
Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. New bioactive plant heliannuols from cultivar sunflower leaves. J. Nat. Prod., 1999, 62, 1636-1639.
[http://dx.doi.org/10.1021/np990249y]
[36]
Macías, F.A.; Oliva, R.M.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Allelochemicals from sunflower leaves cv. Peredovick. Phytochemistry, 1999, 52, 613-621.
[http://dx.doi.org/10.1016/S0031-9422(99)00141-7]
[37]
Macías, F.A.; Torres, A.; Galindo, J.L.G.; Varela, R.M.; Álvarez, J.A.; Molinillo, J.M.G. Bioactive terpenoids from sunflower leaves cv. Peredovick. Phytochemistry, 2002, 61(6), 687-692.
[http://dx.doi.org/10.1016/S0031-9422(02)00370-9] [PMID: 12423890]
[38]
Casas, L.; Mantell, C.; Rodríguez, M.; Torres, A.; Macías, F.A.; Ossa, E.J.M. Identification of major compounds extracted by supercritical fluids from Helianthus annuus L leaves. Solvent Extr. Res. Dev. Jpn., 2011, 18, 55-68.
[http://dx.doi.org/10.15261/serdj.18.55]
[39]
Spring, O.; Pfannstiel, J.; Klaiber, I.; Conrad, J.; Beifuß, U.; Apel, L.; Aschenbrenner, A.K.; Zipper, R. The nonvolatile metabolome of sunflower linear glandular trichomes. Phytochemistry, 2015, 119, 83-89.
[http://dx.doi.org/10.1016/j.phytochem.2015.09.007] [PMID: 26412774]
[40]
Spring, O.; Rodon, U.; Macías, F.A. Sesquiterpenes from noncapitate glandular trichomes of Hellanthus annuus. Phytochemistry, 1992, 31, 1541-1544.
[http://dx.doi.org/10.1016/0031-9422(92)83102-5]
[41]
Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Potential allelopathic activity of natural plant heliannanes: A proposal of absolute configuration and nomenclature. J. Chem. Ecol., 2000, 26, 2173-2186.
[http://dx.doi.org/10.1023/A:1005524601019]
[42]
Macías, F.A.; Varela, R.M.; Torres, A.; Molinillo, J.M.G. Potential allelopathic guaianolides from cultivar sunflower leaves, var. SH-222*. Phytochemistry, 1993, 34, 669-674.
[http://dx.doi.org/10.1016/0031-9422(93)85337-Q]
[43]
Macías, F.A.; Galindo, J.C.G.; Molinillo, J.M.G.; Castellano, D.; Velasco, R.F.; Chinchilla, D. Developing new herbicide models from allelochemicals. Pestic. Sci., 1999, 55, 633-675.
[http://dx.doi.org/10.1002/(SICI)1096-9063(199906)55:6<662::AID-PS3>3.0.CO;2-Q]
[44]
Doi, F.; Ohara, T.; Ogamino, T.; Sugai, T.; Higashinakasu, K.; Yamada, K.; Shigemori, H.; Hasegawa, K.; Nishiyama, S. Plant-growth inhibitory activity of heliannuol derivatives. Phytochemistry, 2004, 65(10), 1405-1411.
[http://dx.doi.org/10.1016/j.phytochem.2004.03.035] [PMID: 15231414]
[45]
Munoz-Suano, A.; Chinchilla, D.; Aguilar, S.; Molinillo, J.M.; Macias, F.A.; Rodríguez-Iglesias, M.A.; Garcia-Cozar, F. Sesquiterpenes as immunosuppressants. Transplantation, 2009, 88(3)(Suppl.), S24-S30.
[http://dx.doi.org/10.1097/TP.0b013e3181af66fa] [PMID: 19667958]
[46]
Grimm, E.L.; Levac, S.; Trimble, L.A. Total synthesis of (±) heliannuol A. Tetrahedron Lett., 1994, 35, 6847-6850.
[http://dx.doi.org/10.1016/0040-4039(94)85020-8]
[47]
Tuhina, K.; Bhowmik, D.R.; Venkateswaran, R.V. Formal syntheses of heliannuols A and D, allelochemicals from Helianthus annus. Chem. Commun. (Camb.), 2002, (6), 634-635.
[http://dx.doi.org/10.1039/b200103a] [PMID: 12120159]
[48]
Lecornué, F.; Ollivier, J. Convergent formal synthesis of (±)-heliannuols A, K, and L from a common intermediate. Synlett, 2004, 9, 1613-1615.
[49]
Biswas, B.; Sen, P.K.; Venkateswaran, R.V. Bargellini condensation of coumarins. Expeditious route to o-carboxyvinylphenoxyiso-butyric acids and application to the synthesis of sesquiterpenes helianane, heliannuol A and heliannuol C. Tetrahedron, 2007, 63, 12026-12036.
[http://dx.doi.org/10.1016/j.tet.2007.09.006]
[50]
Macías, F.A.; Chinchilla, D.; Molinillo, J.M.G.; Fronczek, F.R.; Shishido, K. A stereoselective route towards heliannuol A. Tetrahedron, 2008, 64, 5502-5508.
[http://dx.doi.org/10.1016/j.tet.2008.03.105]
[51]
Ghosh, S.; Tuhina, K.; Bhowmik, D.R.; Venkateswaran, R.V. Synthesis of heliannuols A and K, allelochemicals from cultivar sunflowers and the marine metabolite helianane, unusual sesquiterpenes containing a benzoxocane ring system. Tetrahedron, 2007, 63, 644-651.
[http://dx.doi.org/10.1016/j.tet.2006.11.014]
[52]
Takabatake, K.; Nishi, I.; Shindo, M.; Shishido, K. Enantioselective total synthesis of heliannuols D and A. J. Chem. Soc., Perkin Trans. 1, 2000, 1807-1808
[http://dx.doi.org/10.1039/b003553j]
[53]
Gallagher, B.D.; Taft, B.R.; Lipshutz, B.H. Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives. Org. Lett., 2009, 11(23), 5374-5377.
[http://dx.doi.org/10.1021/ol9020404] [PMID: 19877705]
[54]
Kishuku, H.; Shindo, M.; Shishido, K. Enantioselective total synthesis of (-)-heliannuol A. Chem. Commun. (Camb.), 2003, (3), 350-351.
[http://dx.doi.org/10.1039/b211227b] [PMID: 12613607]
[55]
Kanematsu, M.; Soga, K.; Manabe, Y.; Morimoto, S.; Yoshida, M.; Shishido, K. Efficient and enantioselective total syntheses of heliannuols A and K. Tetrahedron, 2011, 67, 4758-4766.
[http://dx.doi.org/10.1016/j.tet.2011.05.034]
[56]
Roy, A.; Biswas, B.; Sen, P.K.; Venkateswaran, R.V. Total synthesis of heliannuol B, an allelochemical from Helianthus annuus. Tetrahedron Lett., 2007, 48, 6933-6936.
[http://dx.doi.org/10.1016/j.tetlet.2007.07.177]
[57]
Zhang, J.; Wang, X.; Wang, W.K.; Quan, W.; She, X.; Pan, X. Asymmetric syntheses of heliannuols B and D. Tetrahedron, 2007, 63, 6990-6995.
[http://dx.doi.org/10.1016/j.tet.2007.05.034]
[58]
Manabe, Y.; Kanematsu, M.; Yokoe, H.; Yoshida, M.; Shishido, K. Concise total syntheses of heliannuols B and D. Tetrahedron, 2014, 70, 742-748.
[http://dx.doi.org/10.1016/j.tet.2013.11.070]
[59]
Vyvyan, J.R.; Oaksmith, J.M.; Parks, B.W.; Peterson, E.M. Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement. Tetrahedron Lett., 2005, 46, 2457-2460.
[http://dx.doi.org/10.1016/j.tetlet.2005.02.053]
[60]
Biswas, B.; Sen, P.K.; Venkateswaran, R.V. The synthesis of heliannuol C, an allelochemical from Helianthus annuus. Tetrahedron Lett., 2006, 47, 4019-4021.
[http://dx.doi.org/10.1016/j.tetlet.2006.04.011]
[61]
Kamei, T.; Shindo, M.; Shishido, K. First enantioselective total synthesis of (−)-heliannuol C. Tetrahedron Lett., 2003, 44, 8505-8507.
[http://dx.doi.org/10.1016/j.tetlet.2003.09.086]
[62]
Biswas, B.; Sen, P.K.; Roy, A. Synthesis of (±) heliannuol C. Synth. Commun., 2017, 47, 1692-1701.
[http://dx.doi.org/10.1080/00397911.2017.1344860]
[63]
Vyvyan, J.R.; Looper, R.E. Total synthesis of (±)-heliannuol D, an allelochemical from Helianthus annuus. Tetrahedron Lett., 2000, 41, 1151-1154.
[http://dx.doi.org/10.1016/S0040-4039(99)02284-4]
[64]
Macías, F.A.; Chinchilla, D.; Molinillo, J.M.G.; Marín, D.; Varela, R.M.; Torres, A. Synthesis of heliannane skeletons. Facile preparation of (±)-heliannuol D. Tetrahedron, 2003, 59, 1679-1683.
[http://dx.doi.org/10.1016/S0040-4020(03)00134-0]
[65]
Sabui, S.K.; Venkateswaran, R.V. Synthesis of heliannuol D, an allelochemical from Helianthus annuus. Tetrahedron Lett., 2004, 45, 983-985.
[http://dx.doi.org/10.1016/j.tetlet.2003.11.098]
[66]
Sabui, S.K.; Venkateswaran, R.V. A short, rapid synthesis of heliannuol D, an allelochemical from Helianthus annuus employing ring-closing metathesis. Tetrahedron Lett., 2004, 45, 2047-2048.
[http://dx.doi.org/10.1016/j.tetlet.2004.01.085]
[67]
Vyvyan, J.R.; Loitz, C.; Looper, R.E.; Mattingly, C.S.; Peterson, E.A.; Staben, S.T. Synthesis of aromatic bisabolene natural products via palladium-catalyzed cross-couplings of organozinc reagents. J. Org. Chem., 2004, 69(7), 2461-2468.
[http://dx.doi.org/10.1021/jo035778s] [PMID: 15049646]
[68]
Osaka, M.; Kanematsu, M.; Yoshida, M.; Shishido, K. Synthesis of (±)-heliannuol D based on platinum catalyzed regioselective addition of arylboronic acids to allenes. Heterocycles, 2010, 80, 1003-1012.
[http://dx.doi.org/10.3987/COM-09-S(S)75]
[69]
Zhang, T.; Huang, L.Z.; Li, Y.Q.; Xu, Y.M.; Du, Z.T. A facile synthesis of (+/-)-heliannuol-D. Nat. Prod. Commun., 2013, 8(9), 1197-1200.
[http://dx.doi.org/10.1177/1934578X1300800902] [PMID: 24273844]
[70]
Kishuku, H.; Yoshimura, T.; Kakehashi, T.; Shindo, M.; Shishido, K. Enantiocontrolled total syntheses of (+)-heliannuol D via palladium-mediated heterocyclization. Heterocycles, 2003, 61, 125-131.
[http://dx.doi.org/10.3987/COM-03-S4]
[71]
Manabe, Y.; Kanematsu, M.; Osaka, M.; Yoshida, M.; Shishido, K. Highly efficient, enantiocontrolled total syntheses of (+)-heliannuol D and (-)-helibisabonol A. Heterocycles, 2014, 88, 441-452.
[http://dx.doi.org/10.3987/COM-13-S(S)50]
[72]
Osaka, M.; Kanematsu, M.; Yoshida, M.; Shishido, K. An efficient total synthesis of (+)-heliannuol D. Tetrahedron Asymmetry, 2010, 21, 2319-2320.
[http://dx.doi.org/10.1016/j.tetasy.2010.08.018]
[73]
Doi, F.; Ogamino, T.; Sugai, T.; Nishiyama, S. Synthesis of bioactive sesquiterpene heliannuol E involving a ring-expansion reaction of spirodienones. Synlett, 2003, 3, 411-413.
[74]
Doi, F.; Ogamino, T.; Sugai, T.; Nishiyama, S. Enantioselective synthesis of heliannuol E; structural consideration of natural molecule. Tetrahedron Lett., 2003, 44, 4877-4880.
[http://dx.doi.org/10.1016/S0040-4039(03)01094-3]
[75]
Sato, K.; Yoshimura, T.; Shindo, M.; Shishido, K. Total synthesis of (-)-heliannuol E. J. Org. Chem., 2001, 66(1), 309-314.
[http://dx.doi.org/10.1021/jo0011437] [PMID: 11429917]
[76]
Kamei, T.; Shindo, M.; Shishido, K. An alternative total synthesis of (-)-heliannuol E. Synlett, 2003, 15, 2395-2397.
[77]
Kamei, T.; Takahashi, T.; Yoshida, M.; Shishido, K. Synthesis of (-)-heliannuol E via mercuric triflate catalysed arylene cyclization. Heterocycles, 2009, 78, 1439-1444.
[http://dx.doi.org/10.3987/COM-09-11649]
[78]
Liu, Y.; Huang, C.; Liu, B. Asymmetric total syntheses of heliannuol E and epi-heliannuol E. Tetrahedron Lett., 2011, 52, 5802-5804.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.131]
[79]
Gao, F.; Carr, J.L.; Hoveyda, A.H. A broadly applicable NHC-Cu-catalyzed approach for efficient, site-, and enantioselective coupling of readily accessible (pinacolato)alkenylboron compounds to allylic phosphates and applications to natural product synthesis. J. Am. Chem. Soc., 2014, 136(5), 2149-2161.
[http://dx.doi.org/10.1021/ja4126565] [PMID: 24467274]
[80]
Morimoto, S.; Shindo, M.; Shishido, K. Enantioselective synthesis of heliannuols G and H. Heterocycles, 2005, 66, 69-73.
[http://dx.doi.org/10.3987/COM-05-S(K)21]
[81]
Morimoto, S.; Shindo, M.; Yoshida, M.; Shishido, K. Syntheses of heliannuols G and H; structure revision of the natural products. Tetrahedron Lett., 2006, 47, 7353-7356.
[http://dx.doi.org/10.1016/j.tetlet.2006.08.014]
[82]
Sarkar, D.; Ghosh, M.K. Stereoselective synthesis of heliannuol G. Tetrahedron Lett., 2017, 58, 4336-4339.
[http://dx.doi.org/10.1016/j.tetlet.2017.09.081]
[83]
Lecornué, F.; Paugam, R.; Ollivier, J. Strategies for the total asymmetric synthesis of heliannuols K and L: Scope and limitations. Eur. J. Org. Chem., 2005, 2589-2598.
[http://dx.doi.org/10.1002/ejoc.200400908]