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A Dialdehyde Cyclization Cascade: An Approach to Pleuromutilin
Author(s) -
Helm Matthew D.,
Da Silva Madeleine,
Sucunza David,
Findley Thomas J. K.,
Procter David J.
Publication year - 2009
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.200905490
Subject(s) - cascade , stereocenter , natural product , aldehyde , combinatorial chemistry , chemistry , stereochemistry , organic chemistry , catalysis , chromatography , enantioselective synthesis
Waiting in line : Aldehyde groups take turns reacting in a SmI 2 ‐mediated cyclization cascade to form the skeleton 2 of the antibacterial natural product pleuromutilin. Two rings and four contiguous stereocenters are constructed during the cascade with complete diastereocontrol.