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ChemInform Abstract: Synthesis of 10-Methyl-δ4-octalins by Diels-Alder Reactions of 2H-Thiopyran Surrogates for 1-Ethenyl-2-methylcyclohexene.

✍ Scribed by D. E. WARD; Y. GAI

Book ID: 101857228
Publisher: John Wiley and Sons
Year: 2010
Weight: 41 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199752118

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✦ Synopsis

Synthesis of 10-Methyl-δ4-octalins by Diels-Alder Reactions of 2H-Thiopyran Surrogates for 1-Ethenyl-2-methylcyclohexene.

-In view of the interest in Diels-Alder reactions of 1-ethenyl-2-methylcyclohexene derivatives as a route to natural product skeletons, the use of the 2H-thiopyran diene surrogate (I) is considered. It leads to a variety of adducts which are converted to products which are synthetically equivalent to octalins. Direct desulfurization of these compounds with Raney-Ni leads to a mixture of products. However, by effecting desulfurization prior to the aldol cyclization as demonstrated for (IIIa), (X), and (XIII), the desired 10-methyl-δ 4-octalins can be obtained. -(WARD, D.

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