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Letters in Organic Chemistry

Author(s): Jesus A. Lujan-Montelongo, Adrian Covarrubias-Zuniga, Moises Romero-Ortega and Jose G. Avila-Zarraga

DOI: 10.2174/157017808785740525

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An Efficient Synthesis of (+/-)-Xanthorrhizol: One Pot Decyanation and Demethylation

Page: [470 - 472] Pages: 3

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Abstract

A new and short total synthesis affording (±)-Xanthorrhizol in 90% overall yield is described. The method comprises three steps: 1) C-alkylation of 3-methoxy-4-methyl-benzylcyanide with 5-iodine-2-methyl-pent-2-ene; 2) Cmethylation of the resulting cyanide; and 3) one-pot decyanation and demethylation carried out by the action of lithium.

Keywords: Xanthorrhizol, total synthesis, α-cyanocarbanion, C-alkylation, decyanation, demethylation, ether cleavage