From toluene to taxol™: Chemoenzymatic and enantiodivergent routes to the AB-ring systems of taxoids and ent-taxoids

Martin G. Banwell; Penny Darmos; Malcolm D. McLeod; David C.R. Hockless

doi:10.1055/s-1998-1801

From toluene to taxol™: Chemoenzymatic and enantiodivergent routes to the AB-ring systems of taxoids and ent-taxoids

Martin G. Banwell^*, Penny Darmos, Malcolm D. McLeod, David C.R. Hockless

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

The cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure bicyclo[5.3.1]undecanes 20 and 33 which correspond to the AB-ring systems of ent-taxoids and taxoids, respectively.

Original language	English
Pages (from-to)	897-899
Number of pages	3
Journal	Synlett
Issue number	8
DOIs	https://doi.org/10.1055/s-1998-1801
Publication status	Published - Aug 1998

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title = "From toluene to taxol{\texttrademark}: Chemoenzymatic and enantiodivergent routes to the AB-ring systems of taxoids and ent-taxoids",

abstract = "The cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure bicyclo[5.3.1]undecanes 20 and 33 which correspond to the AB-ring systems of ent-taxoids and taxoids, respectively.",

author = "Banwell, \{Martin G.\} and Penny Darmos and McLeod, \{Malcolm D.\} and Hockless, \{David C.R.\}",

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AU - Banwell, Martin G.

AU - Darmos, Penny

AU - McLeod, Malcolm D.

AU - Hockless, David C.R.

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N2 - The cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure bicyclo[5.3.1]undecanes 20 and 33 which correspond to the AB-ring systems of ent-taxoids and taxoids, respectively.

AB - The cis-1,2-dihydrocatechol 2 has been converted, via reaction sequences including Diels-Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure bicyclo[5.3.1]undecanes 20 and 33 which correspond to the AB-ring systems of ent-taxoids and taxoids, respectively.

UR - https://www.scopus.com/pages/publications/0002430104

U2 - 10.1055/s-1998-1801

DO - 10.1055/s-1998-1801

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JO - Synlett

JF - Synlett

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ER -

From toluene to taxol™: Chemoenzymatic and enantiodivergent routes to the AB-ring systems of taxoids and ent-taxoids

Abstract

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