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Biomimetic Total Synthesis of (+)‐Gelsemine
Author(s) -
Zhou Xuan,
Xiao Tao,
Iwama Yusuke,
Qin Yong
Publication year - 2012
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/anie.201201736
Subject(s) - oxonium ion , stereocenter , ring (chemistry) , aziridine , enol , cascade reaction , stereochemistry , chemistry , enantioselective synthesis , organic chemistry , ion , catalysis
Challenging : (+)‐gelsemine was synthesized from ( R , R )‐aziridine 1 in 25 steps with approximately 1 % overall yield. A multistep, one‐pot enol–oxonium cyclization cascade was used to construct, simultaneously, the E ring, F ring, C3 stereocenter, and C7 quaternary stereocenter. This synthesis using the enol–oxonium cyclization reaction as a key step to make the cage structure has demonstrated the proposed biosynthetic pathway of the gelsemine family.