479485-03-5Relevant articles and documents
Total synthesis of epothilone A through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C
Liu, Zhi-Yu,Chen, Ze-G,Yu, Cheng-Zhi,Wang, Rui-Fang,Zhang, Ru-Zhou,Huang, Chu-Sheng,Yan, Zheng,Cao, De-Rong,Sun, Jian-Bo,Li, Gang
, p. 3747 - 3756 (2007/10/03)
The total synthesis of epothilone A is described by the coupling four segments 4 - 7a. Three of the segments, 4, 5 and 7a, have only one chiral center; all other chiral centers were introduced by simple asymmetric catalytic reactions. The key steps are the ring opening of epoxide 5 with acetylide 8 for the construction of the C12-C13 cis double bond and a practical hydrolytic kinetic resolution (HKR) developed by Jacobsen group for the introduction the chiral center at C3. Especially, the stereospecific epoxidation of 3-O-PMB epothilone C 3b through long-range effect of 3-O-PMB protecting group gave high yields of the C12 - C13 α-epoxide for the synthesis of target molecule.