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Enantioselective Total Synthesis of (+)‐Gelsemine: Determination of Its Absolute Configuration
Author(s) -
Yokoshima Satoshi,
Tokuyama Hidetoshi,
Fukuyama Tohru
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001117)39:22<4073::aid-anie4073>3.0.co;2-v
Subject(s) - enantioselective synthesis , pyrrolidine , total synthesis , intramolecular force , absolute configuration , stereochemistry , ring (chemistry) , core (optical fiber) , chemistry , bicyclic molecule , alkaloid , mathematics , organic chemistry , catalysis , computer science , telecommunications
The unique hexacyclic cagelike structure of (+)‐gelsemine ( 1 ) has been accomplished. The first enantioselective total synthesis of this alkaloid features a facile construction of the bicyclo[3.2.1] core by means of two rearrangement reactions and the efficient formation of the pyrrolidine ring by an intramolecular Michael addition. Bn=Benzyl.