Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 29, Pages 9851-9855Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201904404
Keywords
biomimetic synthesis; cycloaddition; metathesis; terpenoids; total synthesis
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Funding
- JSPS KAKENHI [15K05504]
- Naito Foundation
- Grants-in-Aid for Scientific Research [15K05504] Funding Source: KAKEN
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The short, efficient total synthesis of (+)-aquatolide was achieved by a biomimetic transannular [2+ 2] photocycloaddition, and provides the first example of constructing a 5/5/4/8-ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7-ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, ()-asteriscunolides A, C, D, and I, and (+)-tetradehydroasteriscanolide.
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