214892-52-1

Upstream product

• 214892-51-0 (2S,3S)-2-(p-methoxybenzyloxy)-3-(hept-6-enoyl)hex-5-ene 
• 214892-50-9 (4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene 
• 126361-27-1 (S)-(p-methoxybenzyloxy)propanal 
• 122151-36-4 (S)-2-O-(4'-methoxybenzyl)propan-1,2-diol 
• 144401-98-9 (S)-2-(4-methoxybenzyloxy)propionic acid ethyl ester 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 1119-60-4 hept-6-enoic acid 

Downstream Products

• 214892-53-2 (3S,10S)-10-[(1S)-(p-methoxybenzyloxy)ethyl]-3-methyl-3,4,5,6,9,10-hexahydrooxecin-2-one 

Relevant academic research and scientific papers

The formal total synthesis of epothilone A

The formal total synthesis of epothilone A is described. The key steps in the synthesis of the northern hemisphere are a Z-selective ten-membered ring-closing metathesis reaction (RCM) and the diastereoselective alkylation at C8. Aldehyde 3 is formed by introduction of the thiazole moiety by a Wittig reaction and subsequent functional group transformation. An efficient route to keto acid 5 is described.

Improved synthesis of the northern hemisphere of epothilone A by a sharpless asymmetric dihydroxylation

An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner.

Synthesis of the northern hemisphere of epothilone A by a ten-membered ring closing metathesis reaction

The synthesis of the strained epothilone analog containing a ten- membered ring as well as the northern hemisphere of epothilone A is described. This approach, using the ring closing metathesis reaction, is a solution to the lack of stereocontrol observed

Synthesis of the C7-C17 segment of epothilones by a 10-membered ring closing metathesis reaction

The synthesis of the C7-C17 segment of epothilones employing a ring closing metathesis is described. Our approach utilizes the stereoselective methylation of the 10-membered lactone, generated by ring closing metathesis, for introducing the methyl group at C8 and provides an efficient access to strained epothilone derivatives, as well as to the C7-C17 segment of epothilones.