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ChemInform Abstract: Stereoselective Total Synthesis of (.+-.)-Swainsonine Based on endo Mode Cyclization.

✍ Scribed by C. MUKAI; Y. SUGIMOTO; K. MIYAZAWA; S. YAMAGUCHI; M. HANAOKA


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Stereoselective Total Synthesis of (Β±)-Swainsonine Based on endo Mode Cyclization.

-The crucial step in the synthesis of title alkaloid (IX) is the endo mode cyclization of cis epoxide (II) by successive treatment with Co 2 (CO) 8 , Lewis acid, and CAN. The trans-piperidine (III) is formed as major diastereomer with retention of configuration at the propynyl center.


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