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An efficient route to functionalized dienes for decalin synthesis

✍ Scribed by John W. Benbow; Reeti Katoch; Bonnie L. Martinez; Steven B. Shetzline

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 294 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00823-x

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✦ Synopsis

Reaction of the trimethylsilyl (TMS) enol ethers 6 derived from the conjugate addition of organocopper reagents to 3,4-dimethylcyclopentenone with dimethyl dioximne (DMDO) leads to a-hydroxy ketones 7 with predominantly the syn-methyl orientation. Exposure of these systems to metbanolic lead tetraacetate (Pb(OAc),) delivers aldehydic esters 8 which are homologated to the desired E-dienes 9 using Yamamoto's allylic phosphine oxide reagent.

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