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Catalysis-Based Total Synthesis of Latrunculin B

✍ Scribed by Alois Fürstner; Dominic De Souza; Liliana Parra-Rapado; Jon T. Jensen

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
119 KB
Volume
115
Category
Article
ISSN
0044-8249

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✦ Synopsis

Scheme 1. Retrosynthetic analysis of latrunculin B. Scheme 2. Synthesis of two building blocks by iron-catalyzed crosscoupling reactions: a) KHMDS, PhN(Tf) 2 , THF, À 78 8C, 61 %; b) [Fe(acac) 3 ] (10 mol %), THF, À 30 8C, 97 %; c) aqueous NaOH, MeOH, 92 %; d) CDI, THF, 71 %; e) NaH, PMBBr, THF, 77 %; f) aq. KOH, Et 2 O, 98 %; g) 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine, THF, À 18 8C; h) [Fe(acac) 3 ] (1.5 mol %), MeMgBr, THF, À 78 8C!0 8C, 80 %. HMDS = hexamethyldisilazide, Tf = trifluoromethanesulfonyl, acac = acetylacetone, CDI = N,N'-carbonyldiimidazole, PMB = p-methoxybenzyl.

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