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

Martin G. Banwell; Alison J. Edwards; Gwion J. Harfoot; Katrina A. Jolliffe; Malcolm D. McLeod; Kenneth J. McRae; Scott G. Stewart; Markus Vögtle

doi:10.1351/pac200375020223

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

Martin G. Banwell^*, Alison J. Edwards, Gwion J. Harfoot, Katrina A. Jolliffe, Malcolm D. McLeod, Kenneth J. McRae, Scott G. Stewart, Markus Vögtle

^*Corresponding author for this work

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

106 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
Number of pages	7
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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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 = "Banwell, {Martin G.} and Edwards, {Alison J.} and Harfoot, {Gwion J.} and Jolliffe, {Katrina A.} and McLeod, {Malcolm D.} and McRae, {Kenneth J.} and Stewart, {Scott G.} and Markus V{\"o}gtle",

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AU - Banwell, Martin G.

AU - Edwards, Alison J.

AU - Harfoot, Gwion J.

AU - Jolliffe, Katrina A.

AU - McLeod, Malcolm D.

AU - McRae, Kenneth J.

AU - Stewart, Scott G.

AU - Vögtle, Markus

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.

UR - http://www.scopus.com/inward/record.url?scp=0037318016&partnerID=8YFLogxK

U2 - 10.1351/pac200375020223

DO - 10.1351/pac200375020223

M3 - Article

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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

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