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

Jesus   A.   Lujan-Montelongo; Adrian      Covarrubias-Zuniga; Moises      Romero-Ortega; Jose   G.   Avila-Zarraga

doi:10.2174/157017808785740525

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

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Letters in Organic Chemistry

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

Volume: 5 Issue: 6

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

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

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.

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Lujan-Montelongo A. Jesus, Covarrubias-Zuniga Adrian, Romero-Ortega Moises and Avila-Zarraga G. Jose, An Efficient Synthesis of (+/-)-Xanthorrhizol: One Pot Decyanation and Demethylation, Letters in Organic Chemistry 2008; 5 (6) . https://dx.doi.org/10.2174/157017808785740525