Generic placeholder image

Letters in Organic Chemistry

Author(s): Ravi Gurram and Srihari Pabbaraja*

DOI: 10.2174/1570178619666220523094936

DownloadDownload PDF Flyer Cite As
A Convergent Approach for Protected (+)-Paecilomycin F

Page: [185 - 192] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Background: A stereoselective synthetic strategy toward (+)-paecilomycin F is reported. The approach utilizes readily available commercial 2,4,6-trihydroxy benzoic acid and easily accessible chiral R(+)-propylene oxide as starting materials.

Methods: The synthesis involves regioselective Grignard reaction, Wittig reaction, Sharpless asymmetric dihydroxylation, Barbier-type allylation, Stille-coupling and ring-closing metathesis as key reactions.

Results: The target molecule is produced in a 7-step linear sequence with an overall yield of 20% starting from 2,4,6-trihydroxy benzoic acid or a 12-step sequence with an overall yield of 12.95% starting from R(+)-propylene oxide.

Conclusion: The aromatic fragment synthesis was achieved using earlier known protocols starting from 2,4,6-trihydroxy benzoic acid (vide infra).

Keywords: Macrolide, resorcylic acid lactone, metathesis, mitsunobu etherification, sharpless asymmetric dihydroxylation.

Graphical Abstract

[1]
(a) Stob, M.; Baldwin, R.S.; Tuite, J.; Andrews, F.N.; Gillette, K.G. Nature, 1962, 196, 1318.
[http://dx.doi.org/10.1038/1961318a0] [PMID: 13984207];
(b) Bang, S.; Shim, S.H. Arch. Pharm. Res., 2020, 43(11), 1093-1113.
[http://dx.doi.org/10.1007/s12272-020-01275-6] [PMID: 33113097]
[2]
(a) Kim, Y.J.; Lee, S.A.; Myung, S.C.; Kim, W.; Lee, C.S. Mol. Cell. Biochem., 2012, 359(1-2), 33-43.
[http://dx.doi.org/10.1007/s11010-011-0997-9] [PMID: 21800052];
(b) Luo, S.; Wang, T.; Qin, H.; Lei, H.; Xia, Y. Am. J. Physiol. Cell Physiol., 2011, 301(1), C227-C233.
[http://dx.doi.org/10.1152/ajpcell.00493.2010] [PMID: 21430289];
(c) Day, J.E.H.; Sharp, S.Y.; Rowlands, M.G.; Aherne, W.; Lewis, W.; Roe, S.M.; Prodromou, C.; Pearl, L.H.; Workman, P.; Moody, C.J. Chemistry, 2010, 16(34), 10366-10372.
[http://dx.doi.org/10.1002/chem.201001119] [PMID: 20661961]
[3]
(a) Ayers, S.; Graf, T.N.; Adcock, A.F.; Kroll, D.J.; Matthew, S.; Carcache de Blanco, E.J.; Shen, Q.; Swanson, S.M.; Wani, M.C.; Pearce, C.J.; Oberlies, N.H. J. Nat. Prod., 2011, 74(5), 1126-1131.
[http://dx.doi.org/10.1021/np200062x] [PMID: 21513293];
(b) Isaka, M.; Suyarnsestakorn, C.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y. J. Org. Chem., 2002, 67(5), 1561-1566.
[http://dx.doi.org/10.1021/jo010930g] [PMID: 11871887];
(c) Isaka, M.; Yangchum, A.; Intamas, S.; Kocharin, K.; Jones, P.; Kongsaeree, E.B.G.; Prabpai, S. Tetrahedron, 2009, 65, 4396-4403.
[http://dx.doi.org/10.1016/j.tet.2009.03.050];
(d) Hellwig, V.; Mayer-Bartschmid, A.; Müller, H.; Greif, G.; Kleymann, G.; Zitzmann, W.; Tichy, H.V.; Stadler, M. J. Nat. Prod., 2003, 66(6), 829-837.
[http://dx.doi.org/10.1021/np020556v] [PMID: 12828470];
(e) Ayer, W.A.; Lee, S.P.; Tsuneda, A.; Hiratsuka, Y. Can. J. Microbiol., 1980, 26, 766-773.
[http://dx.doi.org/10.1139/m80-133]];
(f) Abid, E.S.; Ouanes, Z.; Hassen, W.; Baudrimont, I.; Creppy, E.; Bacha, H. Toxicol. In Vitro, 2004, 18, 467-474.
[http://dx.doi.org/10.1016/j.tiv.2003.12.011]] [PMID: 15130604];
(g) Furstner, A.; Langemann, K.J. J. Am. Chem. Soc., 1997, 119, 9130-9136.
[http://dx.doi.org/10.1021/ja9719945]];
(h) Kwon, H.J.; Yoshida, M.; Abe, K.; Horinouchi, S.; Beppu, T. Biosci. Biotechnol. Biochem., 1992, 56(3), 538-539.
[http://dx.doi.org/10.1271/bbb.56.538]] [PMID: 1368339];
(i) Chanmugam, P.; Feng, L.; Liou, S.; Jang, B.C.; Boudreau, M.; Yu, G.; Lee, J.H.; Kwon, H.J.; Beppu, T.; Yoshida, M.; Xia, Y.; Wilson, C.B.; Hwang, D. J. Biol. Chem., 1995, 270(10), 5418-5426.
[http://dx.doi.org/10.1074/jbc.270.10.5418] [PMID: 7890656];
(j) Takehara, K.; Sato, S.; Kobayashi, T.; Maeda, T. Biochem. Biophys. Res. Commun., 1999, 257, 19-23.
[http://dx.doi.org/10.1006/bbrc.1999.0401] [PMID: 10092503];
(k) Nonomiya-Tsuji, J.; Kajino, T.; Ono, K.; Ohtomo, T.; Matsumoto, M.; Shiina, M.; Mihara, M.; Tsuchiya, M.; Matsumoto, K. J. Biol. Chem., 2003, 278, 18485-18490.
[http://dx.doi.org/10.1074/jbc.M207453200] [PMID: 12624112];
(l) Dong, J.; Zhu, Y.; Song, H.; Li, R.; He, H.; Liu, H.; Huang, R.; Zhou, Y.; Wang, L.; Cao, Y.; Zhang, K. J. Chem. Ecol., 2007, 33(5), 1115-1126.
[http://dx.doi.org/10.1007/s10886-007-9256-7] [PMID: 17393283]
[4]
(a) Xu, L.; He, Z.; Xue, J.; Chen, X.; Wei, X. J. Nat. Prod., 2010, 73(5), 885-889.
[http://dx.doi.org/10.1021/np900853n] [PMID: 20429578];
(b) Shao, C-L.; Wu, H-X.; Wang, C.Y.; Liu, Q-A.; Xu, Y.; Wei, M-Y.; Qian, P-Y.; Gu, Y-C.; Zheng, C-J.; She, Z-G.; Lin, Y-C. J. Nat. Prod., 2011, 74(4), 629-633.
[http://dx.doi.org/10.1021/np100641b] [PMID: 21348465];
(c) Xu, L.; He, Z.; Xue, J.; Chen, X.; Wei, X. J. Nat. Prod., 2012, 75, 1006-1006.
[http://dx.doi.org/10.1021/np300293b]
[5]
(a) Jana, N.; Nanda, S. Tetrahedron Asymmetry, 2012, 23, 802-808.
[http://dx.doi.org/10.1016/j.tetasy.2012.05.017];
(b) Bhunia, N.; Das, B. Synthesis, 2015, 47, 1499-1509.
[http://dx.doi.org/10.1055/s-0034-1380400]
[6]
Srinivas Reddy, A.; Bhavani, G.; Sandhya, J.; Rajashaker, B.; Subba Reddy, B.V. Nat. Prod. Commun., 2019, 14, 131-133.
[7]
Mohapatra, D.K.; Sai Reddy, D.; Arjunreddy, M.N.; Yadav, J.S. Eur. J. Org. Chem., 2014, 5023-5032.
[http://dx.doi.org/10.1002/ejoc.201402133]
[8]
(a) Singh, S.; Nerella, S.; Pabbaraja, S.; Mehta, G. Org. Lett., 2020, 22(4), 1575-1579.
[http://dx.doi.org/10.1021/acs.orglett.0c00172] [PMID: 32013447];
(b) Mahajan, B.; Mujawar, T.; Ghosh, S.; Pabbaraja, S.; Singh, A.K. Chem. Commun. (Camb.), 2019, 55(79), 11852-11855.
[http://dx.doi.org/10.1039/C9CC06127D] [PMID: 31524906];
(c) Singh, S.; Samineni, R.; Pabbaraja, S.; Mehta, G. Org. Lett., 2019, 21(9), 3372-3376.
[http://dx.doi.org/10.1021/acs.orglett.9b01111] [PMID: 31013110];
(d) Singh, S.; Ramesh, S.; Srihari, P.; Mehta, G. Angew. Chem. Int. Ed., 2018, 57, 16847-16851.
[http://dx.doi.org/10.1002/anie.201810652];
(e) Naresh, G.; Suresh, B.; Srihari, P. Eur. J. Org. Chem., 2018, 1230-1240.
[9]
(a) Srihari, P.; Mahankali, B.; Rajendraprasad, K. Tetrahedron Lett., 2012, 53, 56-58.
[http://dx.doi.org/10.1016/j.tetlet.2011.10.137];
(b) Mahankali, B.; Srihari, P. Eur. J. Org. Chem., 2015, 3983-3993.
[http://dx.doi.org/10.1002/ejoc.201500395]
[10]
Mahankali, B.; Srihari, P. ARKIVOC, 2016, ii, 1-14.
[11]
(a) Kim, J.H.; Scialli, A.R. Toxicol. Sci., 2011, 122(1), 1-6.
[http://dx.doi.org/10.1093/toxsci/kfr088] [PMID: 21507989];
(b) Tokunaga, E.; Yamamoto, T.; Ito, E.; Shibata, N. Sci. Rep., 2018, 8(1), 17131.
[http://dx.doi.org/10.1038/s41598-018-35457-6] [PMID: 30459439]
[12]
(a) Delcamp, J.H.; Gormisky, P.E.; White, M.C. J. Am. Chem. Soc., 2013, 135(23), 8460-8463.
[http://dx.doi.org/10.1021/ja402891m] [PMID: 23701421];
(b) Srihari, P.; Sridhar, Y. Eur. J. Org. Chem., 2011, 2011, 6690-6697.
[http://dx.doi.org/10.1002/ejoc.201100917]
[13]
Das, P.; Babbar, P.; Malhotra, N.; Sharma, M.; Jachak, G.R.; Gonnade, R.G.; Shanmugam, D.; Harlos, K.; Yogavel, M.; Sharma, A.; Reddy, D.S. J. Med. Chem., 2018, 61(13), 5664-5678.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00565] [PMID: 29779382]
[14]
Subba Reddy, B.V.; Janardhan Reddy, P.; Suresh Reddy, C. Tetrahedron Lett., 2013, 54, 5185-5187.
[http://dx.doi.org/10.1016/j.tetlet.2013.07.055]
[15]
Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev., 1994, 94, 2483-2547.
[http://dx.doi.org/10.1021/cr00032a009]
[16]
Petrier, C.; Luche, J.L. J. Org. Chem., 1985, 50, 910-912.
[http://dx.doi.org/10.1021/jo00206a047]
[17]
Altemöller, M.; Gehring, T.; Cudaj, J.; Podlech, J.; Goesmann, H.; Feldmann, C.; Rothenberger, A. Eur. J. Org. Chem., 2009, 2009, 2130-2140.
[http://dx.doi.org/10.1002/ejoc.200801278]
[18]
(a) Mitsunobu, O. Synthesis, 1981, 1-28.
[http://dx.doi.org/10.1055/s-1981-29317];
(b) Kumara Swamy, K.C.; Bhuvan Kumar, N.N.; Balaraman, E.; Pavan Kumar, K.V.P. Chem. Rev., 2009, 109, 2551-2651.
[http://dx.doi.org/10.1021/cr800278z] [PMID: 19382806]
[19]
(a) Stille, J.K. Angew. Chem. Int. Ed. Engl., 1986, 25, 508-524.
[http://dx.doi.org/10.1002/anie.198605081];
(b) Farina, V.; Krishnan, B. J. Am. Chem. Soc., 1991, 113, 9585-9595.
[http://dx.doi.org/10.1021/ja00025a025]
[20]
(a) Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Org. Lett., 1999, 1(6), 953-956.
[http://dx.doi.org/10.1021/ol990909q]] [PMID: 10823227];
(b) Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Angew. Chem. Int. Ed., 2005, 44, 4490-4527.
[http://dx.doi.org/10.1002/anie.200500369]];
(c) White, D.E.; Stewart, I.C.; Grubbs, R.H.; Stoltz, B.M. J. Am. Chem. Soc., 2008, 130(3), 810-811.
[http://dx.doi.org/10.1021/ja710294k]] [PMID: 18163634]