α-Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide - Archive ouverte HAL Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2007

α-Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide

Abstract

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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Dates and versions

hal-03333683 , version 1 (03-09-2021)

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Elsa De lemos, François-Hugues Porée, Alain Commerçon, Jean-François Betzer, Ange Pancrazi, et al.. α-Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide. Angewandte Chemie International Edition, 2007, 46 (11), pp.1917-1921. ⟨10.1002/anie.200604629⟩. ⟨hal-03333683⟩

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