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Total synthesis of (+)-latrunculin A

✍ Scribed by Smith, Amos B.; Noda, Ichio; Remiszewski, Stacy W.; Liverton, Nigel J.; Zibuck, Regina

Book ID
120405046
Publisher
American Chemical Society
Year
1990
Tongue
English
Weight
310 KB
Volume
55
Category
Article
ISSN
0022-3263

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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

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## Abstract The latrunculins are highly selective actin‐binding marine natural products and as such play an important role as probe molecules for chemical biology. A short, concise and largely catalysis‐based approach to this family of bioactive macrolides is presented. Specifically, the macrocycli