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Direct approach to the bakkanes: A synthesis of (±)-homogynolide-B

✍ Scribed by Fernando Coelho; Jean-Pierre Deprés; Timothy J. Brocksom; Andrew E. Greene

Book ID
104227063
Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
159 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

A short synthesis of racemic homogynolide-B is described. The key step of the approach, cycloaddition of dichloroketene with the 2,2-dimethyltrimethylene acetal of 2,3-dimethyl-3-cyclohexen-l-one, proceeds with excellent selectivity and in high yield.

The bakkanes, a relatively small group of hydrindane natural products, 1 have to date received only limited attention from synthetic chemists. In fact, merely a few preparations of bakkenolide-A, the structural prototype of the class, have so far been reported.' In this

Letter we describe the synthesis of homogynolide-B (11, the first synthesis of one of the more highly functionalized bakkanes. Homogynolide-B, isolated from the neutral extracts of the

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✍ Brocksom, Timothy J.; Coelho, Fernando; Deprés, Jean-Pierre; Greene, Andrew E.; 📂 Article 📅 2002 🏛 American Chemical Society 🌐 English ⚖ 364 KB