Exploring biosynthetic relationships among furanocembranoids: Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B

Paul A. Roethle; Paul T. Hernandez; Dirk Trauner

doi:10.1021/ol062581o

Exploring biosynthetic relationships among furanocembranoids: Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B

Paul A. Roethle, Paul T. Hernandez, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

(Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.

Original language	English (US)
Pages (from-to)	5901-5904
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	25
DOIs	https://doi.org/10.1021/ol062581o
State	Published - Dec 7 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.",

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AU - Hernandez, Paul T.

AU - Trauner, Dirk

PY - 2006/12/7

Y1 - 2006/12/7

N2 - (Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.

AB - (Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.

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Exploring biosynthetic relationships among furanocembranoids: Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B

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