327186-71-0

Upstream product

• 100-39-0 benzyl bromide 
• 87479-97-8 (2S,3R)-1,2-epoxy-3-butenol 

Downstream Products

• 479484-93-0 (2R,3S,10S)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-yn-3-ol 
• 443119-47-9 (Z)-(2R,3S,10S)-2-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-10-methyl-undec-5-en-3-ol 
• 479484-94-1 (2R,3S,10S,5Z)-2-benzyloxy-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]undec-5-en-3-ol 
• 443119-46-8 (2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol 

Relevant academic research and scientific papers

Total synthesis of epothilone A through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C

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.

Towards a synthesis of epothilone A: Asymmetric synthesis of C(1)-C(6) and C(7)-C(15) fragments

The asymmetric synthesis of protected C(1)-C(6) and C(7)-C(15) fragments of epothilone A starting from 1,3-cyclohexanedione and methyl L-hydroxy propionate, respectively, is described.