Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors*

M.G. Banwell; A.J. Edwards; G.J. Harfoot; K.A. Jolliffe; M.D. Mcleod; K.J. Mcrae; Scott Stewart; M. Vogtle

doi:10.1351/pac200375020223

Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors*

M.G. Banwell, A.J. Edwards, G.J. Harfoot, K.A. Jolliffe, M.D. Mcleod, K.J. Mcrae, Scott Stewart, M. Vogtle

School of Molecular Sciences

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

107 Citations (Scopus)

Abstract

The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.

Original language	English
Pages (from-to)	223-229
Journal	Pure and Applied Chemistry
Volume	75
Issue number	2-3
DOIs	https://doi.org/10.1351/pac200375020223
Publication status	Published - 2003

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http://iupac.org/publications/pac/

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title = "Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors*",

abstract = "The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.",

author = "M.G. Banwell and A.J. Edwards and G.J. Harfoot and K.A. Jolliffe and M.D. Mcleod and K.J. Mcrae and Scott Stewart and M. Vogtle",

year = "2003",

doi = "10.1351/pac200375020223",

language = "English",

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pages = "223--229",

journal = "Pure and Applied Chemistry",

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T1 - Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors*

AU - Banwell, M.G.

AU - Edwards, A.J.

AU - Harfoot, G.J.

AU - Jolliffe, K.A.

AU - Mcleod, M.D.

AU - Mcrae, K.J.

AU - Stewart, Scott

AU - Vogtle, M.

PY - 2003

Y1 - 2003

N2 - The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.

AB - The enantiomerically pure cis-1,2-dihydrocatechols 2, which are generated by enzymatic dihydroxylation of the corresponding aromatic, engage in regio- and stereo-controlled Diels-Alder cycloaddition reactions to give a range of synthetically useful bicyclo[2.2.2]octenes. Certain examples of the latter type of compound have been used as starting materials in the synthesis of the sesquiterpenoids (-)-patchoulenone and (-)-hirsutene.

U2 - 10.1351/pac200375020223

DO - 10.1351/pac200375020223

M3 - Article

SN - 0033-4545

VL - 75

SP - 223

EP - 229

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 2-3

ER -

Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors*

Abstract

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