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.
Enantioselective synthesis of curacin A. 2. Total synthesis of curacin A by condensation of C1-C7, C8-C17, and C18-C22 segments
Ito, Hisanaka,Imai, Nobuyuki,Takao, Ken-Ichi,Kobayashi, Susumu
, p. 1799 - 1800 (1996)
Total synthesis of curacin A, a novel antimitotic antiproliferative antibiotic, was achieved by the connection of C1-C7, C8-C17, and C18-C22 segments by Julia coupling and iminoether condensation.
Total synthesis of (+)-curacin A, a novel antimitotic metabolite from a cyanobacterium
Muir, James C.,Pattenden, Gerald,Ye, Tao
, p. 2243 - 2250 (2007/10/03)
A concise total synthesis of (+)-curacin A, a potent antimitotic agent isolated from the cyanobacterium Lyngbya majuscula, is described. The synthesis features a new strategy to the 2-cyclopropyl-4-alkenyl substituted thiazoline unit in the natural product involving facile and selective thioacylation of the amino-alcohol 10 with the benzotriazole derived thioamide 11, leading to 28, as a key step. Cyclodehydration of 28 using Burgess' reagent then completed the synthesis of curacin A 1.
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
Synthetic study on curacin A: A novel antimitotic agent from the cyanobacterium Lyngbya majuscula
Onoda, Toshihiko,Shirai, Ryuichi,Koiso, Yukiko,Iwasaki, Shigeo
, p. 14543 - 14562 (2007/10/03)
Curacin A (1), a novel antimitotic agent, was synthesized in a highly stero-controlled manner. The four stereoisomers of a partial structure at the thiazoline moiety, 2 were also synthesized to aid in elucidation of the absolute configurations of three chiral centers in curacin A. The effects of porcine brain tubulin assembly of several synthetic compounds related to curacin A were examined.
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.
Total synthesis of the antimitotic marine natural product (+)-curacin A
Wipf, Peter,Xu, Wenjing
, p. 6556 - 6562 (2007/10/03)
The structurally novel antimitotic agent curacin A was prepared in 15 steps and in 2.6% yield for the longest linear sequence. Key steps in our synthesis are the use of a hydrozirconation-transmetalation protocol for the preparation of divinyl alcohol 8, the stereoselective formation of the acyclic triene segment 11 via enol triflate chemistry, and a second hydrozirconation of the conjugated triene followed by an isocyanide insertion. For the preparation of the heterocyclic moiety of curacin A, the oxazoline → thiazoline conversion offered an efficient access to the sensitive marine natural product.
Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula
Lai, Jing-Yu,Yu, Jurong,Mekonnen, Belew,Falck
, p. 7167 - 7170 (2007/10/03)
Charette asymmetric cyclopropanation, chiral thiazoline synthesis by thioamide cyclization under modified Mitsunobu conditions, Ti(iPrO)4/bi-naphthol catalyzed allylstannane addition, and an exceptionally mild two-carbon homologation via dehydrative alkylation with phenylsulfonylacetonitrile/Ph3P/ADDP convened in an efficient, stereocontrolled route to the title bioactive heterocycle.
Total synthesis of curacin A
Hoemann, Michael Z.,Agrios, Konstantinos A.,Aube, Jeffrey
, p. 953 - 956 (2007/10/03)
Curacin A (1) was synthesized in a convergent manner. The key steps were (1) a Julia coupling to establish the stereochemistry of the C(7-10) diene, (2) a Wittig reaction to establish the stereochemistry of the C(3-4) alkene, and (3) a dehydrative cyclization to form the thiazoline ring system.
