Synthesis of naturally occurring diene and trienes by Te/Li exchange on (1Z, 3Z)-butyltelluro-4-methoxy-1, 3-butadiene

MJ Dabdoub, VB Dabdoub, ACM Baroni, GR Hurtado…

Index: Dabdoub, Miguel J.; Dabdoub, Vania B.; Baroni, Adriano C.M.; Hurtado, Gabriela R.; Barbosa, Sandro L. Tetrahedron Letters, 2010 , vol. 51, # 13 p. 1666 - 1670

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Citation Number: 10

Abstract

(1Z, 3Z)-Butyltelluro-4-methoxy-1, 3-butadiene 2 was obtained by the hydrotelluration of (Z)- 1-methoxy-but-1-en-3-ynes 1. The butadienyllithium 3 obtained by the Te/Li exchange reaction in the (1Z, 3Z)-1-butyltelluro-4-methoxy-1, 3-butadiene 2 reacted with aldehydes to form the corresponding alcohols 4a–d with total retention of configuration. The alcohols formed undergo hydrolysis, resulting in the α, β, γ, δ-unsaturated aldehydes of (E, E) ...