Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 2, Pages 660-663Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja512527s
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- National Science Foundation [CHE1265964]
- Swiss National Science Foundation
- German Academic Exchange Service (DAAD)
- Direct For Mathematical & Physical Scien [1265964] Funding Source: National Science Foundation
- Division Of Chemistry [1265964] Funding Source: National Science Foundation
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A new concise construction of trans-clerodane diterpenoids is reported in which oxacyclic and trans-hydronaphthalene fragments are coupled, and the critical C9-quaternary carbon stereocenter formed stereoselectively, by 1,6-addition of a tertiary cuprate or a tertiary carbon radical to beta-vinylbutenolide. This strategy is specifically illustrated by total syntheses of (-)-solidagolactone (4), (-)-16-hydroxycleroda-3,13-dien-15,16-olide (5, PL3), and (-)-annonene (6).
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