Addition of Chiral Nucleophiles to Pyridine Compounds: Total Synthesis of (−)‐Isovallesiachotamine and (+)‐Vallesiachotamine | Zendy

Amann Robert | Zendy; Spitzner Dietrich | Zendy

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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.

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