380605-86-7Relevant articles and documents
Total syntheses of epothilones B and D
Jung, Jae-Chul,Kache, Rajashaker,Vines, Kimberly K.,Zheng, Yan-Song,Bijoy, Panicker,Valluri, Muralikrishna,Avery, Mitchell A.
, p. 9269 - 9284 (2007/10/03)
A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.
Total synthesis of epothilone B
Valluri, Muralikrishna,Hindupur, Rama M.,Bijoy, Panicker,Labadie, Guillermo,Jung, Jae-Chul,Avery, Mitchell A.
, p. 3607 - 3609 (2007/10/03)
Figure presented Epothilone A, 1, R = H Epothilone B, 2, R = Me A convergent and stereoselective total synthesis of epothilone B (2) is described. The key steps are Normant reaction, Wadsworth-Emmons reaction of a methyl ketone 14 with the phosphonate reagent 7, diastereoselective aldol condensation of aldehyde 3 with enolate 4 to form the C6-C7 bond, and macrolactonization.
