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Book Sections Year : 2015

Discodermolide : Total Synthesis of Natural Product and Analogues

Abstract

This account describes an efficient and modulable total synthesis of (+)-discodermolide and analogues. Particularly notable is the repeated application of a crotylation reaction of aldehydes, with α-oxygenated crotyltitanium reagent to ensure the stereocontrolled elaboration of syn–anti methyl-hydroxy-methyl triads connected to a Z-O-enecarbamate. This particular group allowed direct and easy access to either a triple bond or terminal Z-diene function. The stereocontrolled generation of the trisubstituted Z-double bond, representing a significant synthetic challenge, is ensured by a 1,2-dyotropic rearrangements on dihydrofuran with organocopper reagents. The synthesis of natural product was achieved in 21 steps with 1.6% overall yield. The same methodologies and synthetic strategy were applied for the preparation of five original analogues. The biological activities of natural product and synthetic analogues have also been studied.
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hal-02152301 , version 1 (20-09-2019)

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Janick Ardisson, Jean-François Betzer. Discodermolide : Total Synthesis of Natural Product and Analogues. Michael Harmata. Strategies and Tactics in Organic Synthesis, 11, Elsevier, pp.51-84, 2015, 9780081000236. ⟨10.1016/B978-0-08-100023-6.00003-8⟩. ⟨hal-02152301⟩
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