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

87 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

Access to Document

10.1016/j.tetlet.2006.06.150

Cite this

@article{9d9c22cb8d404e77b2083e53e02a2663,

title = "A biomimetic total synthesis of (+)-intricarene",

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.",

author = "Bencan Tang and Bray, {Christopher D.} and Gerald Pattenden",

year = "2006",

month = sep,

day = "4",

doi = "10.1016/j.tetlet.2006.06.150",

language = "English",

volume = "47",

pages = "6401--6404",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "36",

}

TY - JOUR

T1 - A biomimetic total synthesis of (+)-intricarene

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.

UR - http://www.scopus.com/inward/record.url?scp=33746635066&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.06.150

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this