308357-65-5

Upstream product

• 308357-53-1 (5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one 
• 263900-30-7 (-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 308357-64-4 (2S)-2-methyl-4-(phenylsulfonyl)butanal 
• 121587-29-9 (3S)-3-methyl-1-phenylsulfonylbutan-4-ol 
• 78186-80-8 3,3-dimethyl-4-oxohex-1-ene 
• 308357-54-2 (+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one 

Downstream Products

• 308357-55-3 (4S,7R,8S,9S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9-tetramethyl-11-(phenylsulfonyl)undec-1-en-6-one 

Relevant academic research and scientific papers

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.