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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 18
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Original Articles

Models for Taxol Biosynthesis: SeO2 Oxidation of Taxadiene

Qiulong Huang Department of Chemistry, Texas A & M University, College Station, Texas, USA
,
James D. Pennington Department of Chemistry, Texas A & M University, College Station, Texas, USA
,
Howard J. Williams Department of Chemistry, Texas A & M University, College Station, Texas, USA
&
A. Ian Scott Department of Chemistry, Texas A & M University, College Station, Texas, USACorrespondence[email protected]
Pages 2577-2585 | Received 14 Mar 2006, Published online: 16 Feb 2007
 
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Abstract

Together with the expected mono‐oxidized taxa‐4(20),11(12)‐diene‐5‐ol (1) and taxa‐4(5),11,20‐diene‐20‐ol (2), a new taxane skeleton, 3,12‐cyclotaxane (3), was obtained from chemical oxidation of taxadiene by selenium dioxide/t‐butylhydroperoxide.

Acknowledgment

We thank the Robert A. Welch Foundation and the Texas Advanced Technology Program for financial support and Rodney Croteau for a gift of the gene‐encoding taxadiene synthase.

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