α‐Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide | Zendy

de Lemos Elsa | Zendy; Porée FrançoisHugues | Zendy; Commerçon Alain | Zendy; Betzer JeanFrançois | Zendy; Pancrazi Ange | Zendy; Ardisson Janick | Zendy

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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.

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