The synthesis of 3-spirooxindole derivatives. VII. Total synthesis of alkaloids (.+-.)-rhynchophylline and (.+-.)-isorhynchophylline

Autor:	Takeshi Oishi, Yoshio Ban, Masahiko Seto
Rok vydání:	1975
Předmět:	biology Uncaria rhynchophylla Hydrochloride Sodium chemistry.chemical_element Total synthesis General Chemistry General Medicine biology.organism_classification chemistry.chemical_compound Rhynchophylline chemistry Drug Discovery Organic chemistry Oxindole
Zdroj:	Chemical and Pharmaceutical Bulletin. 23:2605-2613
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.23.2605
Popis:	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.
Databáze:	OpenAIRE
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