Organic letters

Synthesis of δ-tributylstannyl-α, β, γ, δ-unsaturated aldehydes from pyridines

TD Michels, JU Rhee, CD Vanderwal

Index: Michels, Theo D.; Rhee, Jong Uk; Vanderwal, Christopher D. Organic Letters, 2008 , vol. 10, # 21 p. 4787 - 4790

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Citation Number: 24

Abstract

ABSTRACT Zincke aldehydes, which are readily available from the ring-opening reaction of pyridinium salts, are easily converted into δ-tributylstannyl-r, β, γ, δ-unsaturated aldehydes (stannyldienals) by the action of tributylstannyllithium. This reaction appears to proceed via 1, 6-stannyllithium addition/elimination of lithium dialkylamide. Several stannyldienals of significant utility for the synthesis of polyene natural products have been made by this ...