✦ LIBER ✦

Total Synthesis of (±)-N-Acetylcolchinol

✍ Scribed by J.Scott Sawyer; Timothy L. Macdonald

Book ID: 104216720
Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 258 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)80622-x

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✦ Synopsis

An efficient synthesis of the colchicine degradation product N-acetylcolchinol 1 is described featuring a thallium(lIl)-mediated intramolecular non-phenolic biaryl oxidative coupling reaction of intermediate U as the key step. Both the synthetic sample and that obtained from the degradation of colchicine were found to exist in solution as a 3:l mixture of conformational isomers at room temperature.

Current interest in the biological properties of the Colchicum alkaloids is evidenced by numerous recent reports concerning the synthesis and pharmacological evaluation of structural analogs of colchicine 1.2.3 An interesting structure in this regard is the colchicine degradation product N-acetylcolchinol3, first described by Windaus4a in 1914.

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