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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 9
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Original Articles

Oxidation Products of Phenolic Thiocolchicines: Ring a Quinones and Dienones

Jian Guan Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599
,
Arnold Brossi Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599
,
Xiao-Kang Zhu Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599
,
Hui-Kang Wang Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599
&
Kuo-Hsiung Lee Natural Products Laboratory, School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599
Pages 1585-1591 | Received 27 Oct 1997, Published online: 22 Aug 2006
 
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Abstract

An improved, highly selective demethylation of thiocolchicine (1) to the diphenol 5 is described. Oxidation of 2 to para-quinone 6 and of 4 and 5 to ortho-quinones 8 and 10 is first reported. Also, 2-demethylthiocolchicine (3) was oxidized to the quinone methide 7.

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