Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 43, Issue 1, Pages 313-319Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202206034
Keywords
colchicine; (-)-N-acetylcolchinol methyl ether; tert-butanesulfinamide; asymmetric synthesis
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(-)-Colchicine and (-)-N-acetylcolchinol methyl ether were synthesized using a concise asymmetric synthetic approach. The carbon framework was constructed through Aldol condensation of simple aldehydes and ketones, followed by the economical and efficient synthesis of chiral amine intermediates through asymmetric reductive amination with chiral tert-butanesulfinamide. The 3-rings skeleton of colchicine and related alkaloids was then constructed by oxidation with hypervalent iodine reagent. This strategy provides an efficient method for the convenient and economical synthesis of these alkaloids.
(-)-Colchicine and its natural analogue (-)-N-acetylcolchinol methyl ether have been synthesized in a com-paratively conciser asymmetric synthetic approach. Firstly, the carbon framework was constructed by Aldol condensation of simple aldehydes and ketones, and then the chiral amine intermediates were synthesized economically and efficiently through asymmetric reductive amination with chiral tert-butanesulfinamide. The 3-rings skeleton of colchicine and related alkaloids was then constructed by oxidation with hypervalent iodine reagent. Our strategy provides an efficient method for the convenient and economical synthesis of these alkaloids.
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