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Stereochemistry and cycloaddition of 1,1,3-trioxy butadienes from β-keto esters

✍ Scribed by Stephen H. Bell; Donald W. Cameron; Geoffrey I. Feutrill; Brian W. Skelton; Allan H. White

Book ID
104229194
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
287 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Spectroscopic analysis of the 1,1,3-trioxy dienes (l), (2) shows them to possess @)-stereochemistry, contrary to several literature assignments; characterisation of derived cycloadducts and crystallographic analysis of one of them (20) establishes endo cycloaddition. Cycloaddition of polyoxygenated butadienes to quinones and other dienophiles finds extensive use in synthesis of polycyclic compounds', such dienes being conveniently accessible by O-silylation of ketone or ester enolates2. The 1,1,3-trioxy dienes (l), (2) derived from methyl acetoacetate are of particular interest since they give the 1,3-dioxy system of polyketides following cycloaddition and subsequent aromatisation. We3 and others4'5 earlier

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