A chemoenzymatic synthesis of (−)-hirsutene from toluene

Martin G. Banwell; Alison J. Edwards; Gwion J. Harfoot; Katrina A. Jolliffe

doi:10.1039/b208778b

A chemoenzymatic synthesis of (−)-hirsutene from toluene

Martin G. Banwell^*, Alison J. Edwards, Gwion J. Harfoot, Katrina A. Jolliffe

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of toluene, has been converted, via a sequence of reactions including high-pressure promoted Diels–Alder cycloaddition and oxa-di-Π-methane rearrangement steps, into the triquinane (−)-hirsutene (1).

Original language	English
Pages (from-to)	2439-2441
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
Volume	2
Issue number	22
DOIs	https://doi.org/10.1039/b208778b
Publication status	Published - 12 Sept 2002

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title = "A chemoenzymatic synthesis of (−)-hirsutene from toluene",

abstract = "The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of toluene, has been converted, via a sequence of reactions including high-pressure promoted Diels–Alder cycloaddition and oxa-di-Π-methane rearrangement steps, into the triquinane (−)-hirsutene (1).",

author = "Banwell, \{Martin G.\} and Edwards, \{Alison J.\} and Harfoot, \{Gwion J.\} and Jolliffe, \{Katrina A.\}",

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AU - Banwell, Martin G.

AU - Edwards, Alison J.

AU - Harfoot, Gwion J.

AU - Jolliffe, Katrina A.

PY - 2002/9/12

Y1 - 2002/9/12

N2 - The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of toluene, has been converted, via a sequence of reactions including high-pressure promoted Diels–Alder cycloaddition and oxa-di-Π-methane rearrangement steps, into the triquinane (−)-hirsutene (1).

AB - The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of toluene, has been converted, via a sequence of reactions including high-pressure promoted Diels–Alder cycloaddition and oxa-di-Π-methane rearrangement steps, into the triquinane (−)-hirsutene (1).

UR - https://www.scopus.com/pages/publications/0036027101

U2 - 10.1039/b208778b

DO - 10.1039/b208778b

M3 - Article

SN - 1472-7781

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 22

ER -

A chemoenzymatic synthesis of (−)-hirsutene from toluene

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