Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Synthesis of 3-Spirooxindole Derivatives. VII. Total Synthesis of Alkaloids (±)-Rhynchophylline and (±)-Isorhynchophylline
YOSHIO BANMASAHIKO SETOTAKESHI OISHI
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1975 Volume 23 Issue 11 Pages 2605-2613

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Abstract
The total synthesis of (±)-rhynchophylline (Ia) and (±)-isorhynchophylline (Ib) which are oxindole alkaloids of Uncaria rhynchophylla MIQ (Ourouparia rhynchophylla MATSUM), has been completed through eight stages starting from the condensation of 2-hydroxytryptamine hydrochloride (III) with ethyl sodium formyl acetate (IV). The success in the first-stage condensation is significant since ethyl sodium formyl acetate (IV) is rather unstable and has not been existent as the liberated ester. The sterostructures of the intermediates are discussed and mostly assigned.
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© The Pharmaceutical Society of Japan
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