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Addition of Chiral Nucleophiles to Pyridine Compounds: Total Synthesis of (−)‐Isovallesiachotamine and (+)‐Vallesiachotamine
Author(s) -
Amann Robert,
Spitzner Dietrich
Publication year - 1991
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.199113201
Subject(s) - pyridinium , nucleophile , pyridine , ring (chemistry) , closure (psychology) , chemistry , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , law , political science
An enantiomerically pure skeleton of indol alkaloids can be constructed in a one‐pot procedure by adding chiral nucleophiles such as lithiated 2 to the pyridinium compound 1 and carrying out the Pictet–Spengler ring closure according to Wenkert . The product of this reaction has five chiral centers and can be transformed into the title compounds in few steps.