Dihydrocolchicine 8,12-Endoperoxide: A Novel Starting Material for Convenient Syntheses of the AllocolchicinoidsN-AcetylcolchinolO-Methyl Ether and Androbiphenyline
✍ Scribed by Brecht, René ;Haenel, Frank ;Seitz, Gunther
- Book ID
- 102366887
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 477 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
colchicine analogues I Endoperoxide transformations I Colchicine-allocolchicine rearrangement I Axial chirality I Biaryls I Alkaloids I Colchicum autumnale
Optically pure dihydrocolchicine-8,12-endoperoxide 2 is used as the starting material for the synthesis of some bioactive allocolchicinoids. Depending on the reaction conditions and reagents employed, different modifications of the C ring of colchicine (1) are achieved. Triphenylphosphane deoxygenation of 2 leads to the well known N-acetylcolchinol 0methyl ether (NCME, 6, 40% yield from 1). Treatment of the endoperoxide 2 with CH,OH/CH,Cl,/silica gel provides the plant alkaloid androbiphenyline (11) in a yield of 60% from