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Total Synthesis of (−)‐Lycoposerramine‐S
Author(s) -
Shimada Naoaki,
Abe Yuzo,
Yokoshima Satoshi,
Fukuyama Tohru
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.201206863
Subject(s) - stereoselectivity , amide , intramolecular force , alkylation , total synthesis , core (optical fiber) , cycloaddition , computer science , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , telecommunications , catalysis
To the core : The first total synthesis of (−)‐lycoposerramine‐S has been accomplished in 14 steps. The synthesis features the facile construction of the tetracyclic core through an intramolecular 1,3‐dipolar cycloaddition of an azomethine ylide, with unexpected stereoselectivity, an 5‐ exo ‐ trig radical cyclization, and an alkylation of p ‐nosyl (Ns) amide. TBS= tert ‐butyldimethylsilyl.