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An Enantioselective Total Synthesis of (−)‐Isoschizogamine
Author(s) -
Xu Zhengren,
Bao Xu,
Wang Qian,
Zhu Jieping
Publication year - 2015
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.201508150
Subject(s) - enantioselective synthesis , stereocenter , iminium , chemistry , alkylation , stereochemistry , total synthesis , domino , iodide , imine , organic chemistry , catalysis
A concise enantioselective total synthesis of (−)‐isoschizogamine, a complex bridged polycyclic monoterpene indole alkaloid, was accomplished. N‐Alkylation of an enantio‐enriched imine with an alkyl iodide afforded an iminium salt, which, upon heating by microwave irradiation in the presence of pivalic acid, was converted into the hexacyclic structure of natural product by a complex but ordered domino sequence. The one‐pot process leading to the formation of one CC bond and three CN bonds created three rings and three contiguous stereogenic centers with complete control of both the relative and absolute stereochemistry.