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

Martin G. Banwell; Penny Darmos; David C. R. Hockless

doi:10.1071/ch03164

RESEARCH ARTICLE

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

Martin G. Banwell, Penny Darmos and David C. R. Hockless

Australian Journal of Chemistry 57(1) 41 - 52
Published: 05 January 2004

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.

Keywords: anionic oxy-Cope rearrangement — cis-1,2-dihydrocatechols — Diels-Alder reactions — natural products — Taxinine

https://doi.org/10.1071/CH03164

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

Abstract

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