Expedient Synthesis of (±)-Bipinnatin J

Expedient Synthesis of (±)-Bipinnatin J

A nine-step, stereoselective synthesis of bipinnatin J is described, which features a ruthenium-catalyzed Alder-ene reaction, a Stille cross coupling, and an intramolecular Nozaki−Hiyama−Kishi allylation as key steps. The biosynthetic relationship between bipinnatin J and complex polycyclic diterpen...

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Veröffentlicht in:Organic letters 2006-01, Vol.8 (2), p.345-347
Hauptverfasser: Roethle, Paul A, Trauner, Dirk
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Anthozoa - chemistry
Catalysis
Diterpenes - chemical synthesis
Diterpenes - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:A nine-step, stereoselective synthesis of bipinnatin J is described, which features a ruthenium-catalyzed Alder-ene reaction, a Stille cross coupling, and an intramolecular Nozaki−Hiyama−Kishi allylation as key steps. The biosynthetic relationship between bipinnatin J and complex polycyclic diterpenes isolated from gorgonian corals is discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052922i