396092-62-9

Upstream product

• 3282-30-2 pivaloyl chloride 
• 396092-61-8 (4E,7Z)-(2R,3S)-9-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-3,7-dimethyl-nona-4,7-dien-1-ol 
• 88920-24-5 p-methoxybenzyloxy acetic acid 
• 396092-24-3 methyl (2R,3S,10S,4E,7Z)-3,7-dimethyl-10,11-(dimethylmethylene)dioxy-2-(4-methoxybenzyl)oxyundeca-4,7-dienoate 
• 396092-23-2 (4R,9S,2E,6Z)-9,10-(dimethylmethylene)dioxy-6-methyldeca-2,6-dien-4-yl 2-(4-methoxybenzyloxy)acetate 
• 396092-19-6 (2S)-1-tert-butyldimethylsilyloxy-5-methyl-4-(phenylsulfonyl)hex-5-en-2-ol 
• 396092-48-1 (4R,9S,2E,6Z)-9,10-(dimethylmethylene)dioxy-6-methyldeca-2,6-dien-4-ol 
• 396092-18-5 (2S)-5-methyl-4-(phenylsulfonyl)hex-5-ene-1,2-diol 
• 396092-22-1 (2S,7R,4Z,8E)-5-methyldeca-4,8-diene-1,2,7-triol 
• 396092-17-4 (5S)-5,6-(dimethylmethylene)dioxy-2-methylhex-1-en-3-yl phenyl sulfone 

Relevant academic research and scientific papers

Total syntheses of epothilones B and D: Applications of allylstannanes in organic synthesis

Following exploratory studies which culminated in syntheses of the alcohol 16, a total synthesis of epothilones B and D is reported in which the trisubstituted 12,13-double-bond is introduced stereoselectively using the tin(IV) bromide-promoted reaction between the allylstannane 22 and the aldehyde 17. A Barton deoxygenation then gave the C(7)-C(15) fragment 25. After development of the thiazole containing side-chain, an aldol condensation with the ethyl ketone 36 gave the adduct 37 which was taken through to epothilone D 2 and then to epothilone B 1.