A biomimetic total synthesis of (+)-intricarene

Bencan Tang; Christopher D. Bray; Gerald Pattenden

doi:10.1016/j.tetlet.2006.06.150

A biomimetic total synthesis of (+)-intricarene

Bencan Tang, Christopher D. Bray, Gerald Pattenden

Research output: Journal Publication › Article › peer-review

85 Citations (Scopus)

Abstract

An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)₂-^tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo.

Original language	English
Pages (from-to)	6401-6404
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2006.06.150
Publication status	Published - 4 Sept 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.06.150

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abstract = "An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)2-tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo.",

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AU - Tang, Bencan

AU - Bray, Christopher D.

AU - Pattenden, Gerald

PY - 2006/9/4

Y1 - 2006/9/4

N2 - An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)2-tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo.

AB - An asymmetric synthesis of the furanocembrane (-)-bipinnatin J (3a) found in gorgonian corals is described. Treatment of 3a with VO(acac)2-tBuOOH, followed by acetylation, gave acetoxypyranone 15. When 15 was heated in the presence of DBU, it underwent a transannular oxidopyrylium-alkene [5+2] cycloaddition producing the polycyclic diterpene (+)-intricarene 1, isolated from the coral Pseudopterogorgia kallos. The total synthesis of intricarene 1 mimics its most likely biosynthesis via oxidation of bipinnatin J (3a) in vivo.

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DO - 10.1016/j.tetlet.2006.06.150

M3 - Article

AN - SCOPUS:33746635066

SN - 0040-4039

VL - 47

SP - 6401

EP - 6404

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

A biomimetic total synthesis of (+)-intricarene

Abstract

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