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Letter

Expedient Synthesis of (±)-Bipinnatin J

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Paul A. Roethle and Dirk Trauner*

Department of Chemistry, University of California, Berkeley, California 94720

Org. Lett., 2006, 8 (2), pp 345–347

DOI: 10.1021/ol052922i

Publication Date (Web): December 16, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, trauner@cchem.berkeley.edu

Abstract

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.

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Published In Issue January 19, 2006
Received December 1, 2005

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Letter

Expedient Synthesis of (±)-Bipinnatin J

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Exploring Biosynthetic Relationships among Furanocembranoids: Synthesis of (−)-Bipinnatin J, (+)-Intricarene, (+)-Rubifolide, and (+)-Isoepilophodione B

Enantiospecific Total Syntheses of Kapakahines B and F

A Concise, Biomimetic Total Synthesis of (+)-Davanone

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