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Taxane Diterpene Synthesis Studies. Part 1: Chemoenzymatic and Enantiodivergent Routes to AB-ring Substructures of Taxoids and ent -Taxoids

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Date

2004

Authors

Banwell, Martin
Darmos, Penny
Hockless, David

Journal Title

Journal ISSN

Volume Title

Publisher

CSIRO Publishing

Abstract

The microbially derived cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into enantiopure bicyclo[5.3.1]undecenes 21 and 34, which correspond to AB-ring substructures of ent-taxoids and taxoids, respectively.

Description

Keywords

Keywords: Addition reactions; Crystal structure; Enzymes; Ketones; Oxidation; Stereochemistry; Synthesis (chemical); Toluene; Diels Alder cycloaddition; Dihydrocatechol; Enantiodivergent routes; Ent taxoids; Taxane diterpene; Taxoids; Organic compounds

Citation

URI

http://hdl.handle.net/1885/78443

Collections

ANU Research Publications

Source

Australian Journal of Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1071/CH03164

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