155233-30-0Relevant articles and documents
A concise total synthesis of (+)-curacin A, a novel cyclopropyl- substituted thiazoline from the cyanobacterium Lyngbya majuscula
Muir, James C.,Pattenden, Gerald,Ye, Tao
, p. 2861 - 2864 (1998)
A total synthesis of (+)-curacin A 1 which features a facile and selective thioacylation of the polyene amino-alcohol 2 with the benzotriazole-derived cyclopropyl thioamide 3, leading to 15, as a key step is described.
Synthesis of Curacin A: A powerful antimitotic from the cyanobacterium Lyngbya majuscula
White, James D.,Kim, Tae-Seong,Nambu, Mitch
, p. 5612 - 5613 (1995)
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Absolute configuration and total synthesis of (+)-curacin A, an antiproliferative agent from the cyanobacterium Lyngbya majuscula
White, James D.,Kim, Tae-Seong,Nambu, Mitch
, p. 103 - 111 (2007/10/03)
The absolute configuration of curacin A was determined as (2R,13R,19R,21S)-1 by comparison of degradation products 2 and 3 with the same materials prepared by asymmetric synthesis. The total synthesis of 1 was completed from (1R,2S)-2-methylcyclopropaneca
Asymmetric total synthesis of curacin A
Onoda, Toshihiko,Shirai, Ryuichi,Koiso, Yukiko,Iwasaki, Shigeo
, p. 4397 - 4400 (2007/10/03)
Curacin A (1), a novel antimitotic agent, was synthesized in a highly stereo-controlled manner. The key steps were (1) an asymmetric allylation using a chiral allyltitanium reagent and a double-asymmetric Simmons-Smith cyclopropanation to introduce three chiral centers, (2) Wittig and Wittig- Horner reactions to construct the C(3-4) and C(7-10) alkenes, and (3) a direct conversion of the thiazolidine to the thiazoline.
