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α‐Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide
Author(s) -
de Lemos Elsa,
Porée FrançoisHugues,
Commerçon Alain,
Betzer JeanFrançois,
Pancrazi Ange,
Ardisson Janick
Publication year - 2007
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.200604629
Subject(s) - total synthesis , stereochemistry , chemistry , philosophy
A complete strategy : The total synthesis of discodermolide relies on the elaboration of syn – anti stereotriads linked to a Z‐O ‐enecarbamate group, its direct transformation into the terminal Z diene, and stereocontrolled generation of the trisubstituted Z double bond by a dyotropic rearrangement (see scheme; OCb= N , N ‐diisopropylcarbamoyloxy). The synthesis was achieved in 21 steps with 1.6 % overall yield.