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Short, Enantioselective Total Synthesis of Sceptrin and Ageliferin by Programmed Oxaquadricyclane Fragmentation
Author(s) -
Baran Phil S.,
Li Ke,
O'Malley Daniel P.,
Mitsos Christos
Publication year - 2005
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.200503374
Subject(s) - enantiopure drug , enantioselective synthesis , fragmentation (computing) , pyrrole , cyclobutanes , stereochemistry , total synthesis , chemistry , combinatorial chemistry , computer science , organic chemistry , cycloaddition , catalysis , programming language
Absolutely without auxiliaries : The enantioselective syntheses of both enantiomers of the dimeric pyrrole–imidazole alkaloids sceptrin and ageliferin have been achieved by a non‐auxiliary‐based route, which allows assignment of the absolute configuration of natural ageliferin. The “programming” of the oxaquadricyclane fragmentation leading to enantiopure tetrasubstituted cyclobutanes is the crucial step in the synthesis.