Premium
Total Synthesis of the Indole Alkaloid Vallesiachotamine
Author(s) -
Spitzner Dietrich,
Wenkert Ernest
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198409841
Subject(s) - tryptamine , indole test , pyridinium , alkaloid , chemistry , pictet–spengler reaction , total synthesis , indole alkaloid , stereochemistry , organic chemistry , biochemistry
The total syntheses of vallesiachotamine 1 and isovallesiachotamine 2 , indole alkaloids from dogbane plants, which are formed in vitro and in vivo from tryptamine and secologanin, were achieved by addition of silicon‐stabilized anions to pyridinium salts and subsequent Pictet‐Spengler reaction as the key reaction steps. Synthetic 1 and 2 were identical (except in their chiroptic properties) with authentic samples from plant cultures.