The total synthesis of (-)-crispatene

Aubry K. Miller; Daniel H. Byun; Christopher M. Beaudry; Dirk Trauner

doi:10.1073/pnas.0401787101

The total synthesis of (-)-crispatene

Aubry K. Miller, Daniel H. Byun, Christopher M. Beaudry, Dirk Trauner

Chemistry

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

Abstract

The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

Original language	English (US)
Pages (from-to)	12019-12023
Number of pages	5
Journal	Proceedings of the National Academy of Sciences of the United States of America
Volume	101
Issue number	33
DOIs	https://doi.org/10.1073/pnas.0401787101
State	Published - Aug 17 2004

ASJC Scopus subject areas

General

Access to Document

10.1073/pnas.0401787101

Cite this

@article{1ee3ea71617449d5990a22344844a99e,

title = "The total synthesis of (-)-crispatene",

abstract = "The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.",

author = "Miller, {Aubry K.} and Byun, {Daniel H.} and Beaudry, {Christopher M.} and Dirk Trauner",

year = "2004",

month = aug,

day = "17",

doi = "10.1073/pnas.0401787101",

language = "English (US)",

volume = "101",

pages = "12019--12023",

journal = "Proceedings of the National Academy of Sciences of the United States of America",

issn = "0027-8424",

publisher = "National Academy of Sciences",

number = "33",

}

TY - JOUR

T1 - The total synthesis of (-)-crispatene

AU - Miller, Aubry K.

AU - Byun, Daniel H.

AU - Beaudry, Christopher M.

AU - Trauner, Dirk

PY - 2004/8/17

Y1 - 2004/8/17

N2 - The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

AB - The total synthesis of the molluscan polypropionate (-)-crispatene is described. The synthesis features a palladium-catalyzed cross-coupling to establish a sensitive conjugated tetraene and its Lewis acid-catalyzed cycloisomerization to yield the bicyclo[3.1.0]hexene core of the natural product. The absolute configuration of (-)-crispatene and related molecules is established.

UR - http://www.scopus.com/inward/record.url?scp=4344710275&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4344710275&partnerID=8YFLogxK

U2 - 10.1073/pnas.0401787101

DO - 10.1073/pnas.0401787101

M3 - Article

C2 - 15273284

AN - SCOPUS:4344710275

SN - 0027-8424

VL - 101

SP - 12019

EP - 12023

JO - Proceedings of the National Academy of Sciences of the United States of America

JF - Proceedings of the National Academy of Sciences of the United States of America

IS - 33

ER -

The total synthesis of (-)-crispatene

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this