308357-64-4

Upstream product

• 299430-04-9 (S)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane 
• 263900-30-7 (-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone 
• 121587-29-9 (3S)-3-methyl-1-phenylsulfonylbutan-4-ol 

Downstream Products

• 127750-73-6 (9E,13E)-(2R,4S,8S)-6-Benzenesulfonyl-17-(tert-butyl-dimethyl-silanyloxy)-4,8,10,14-tetramethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-octadeca-9,13-dien-5-one 
• 121587-31-3 (4E,8E)-(S)-12-Benzenesulfonyl-4,8,10-trimethyl-dodeca-4,8-dienoic acid methyl ester 
• 121587-32-4 ((4E,8E)-(S)-12-Benzenesulfonyl-1,4,8,10-tetramethyl-dodeca-4,8-dienyloxy)-tert-butyl-dimethyl-silane 
• 127779-23-1 (5E,9E)-(S)-13-Benzenesulfonyl-5,9,11-trimethyl-trideca-5,9-dien-2-ol 
• 121587-30-2 (E)-(S)-8-Benzenesulfonyl-4,6-dimethyl-oct-4-enoic acid methyl ester 
• 127750-72-5 (E)-(S)-10-Benzenesulfonyl-2,6,8-trimethyl-deca-1,6-dien-3-ol 
• 308357-54-2 (+)-(5R,6S,7S)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one 
• 308357-65-5 (4R,5S,6S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,2,4,6-tetramethyl-3-oxo-8-(phenylsulfonyl)octanal 
• 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 
• 308357-53-1 (5R,6S,7S)-6-hydroxy-3,3,5,7-tetramethyl-9-(phenylsulfonyl)non-1-en-4-one 
• 127750-71-4 (S)-6-Benzenesulfonyl-2,4-dimethyl-hex-1-en-3-ol 

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.

TOTAL SYNTHESIS OF A PUTATIVE TRIENE INTERMEDIATE IN MONENSIN BIOSYNTHESIS, ACTIVATED AS A CAPRYLCYSTEAMINE THIOL ESTER.

The total synthesis is reported, from a pool of optically pure starting materials, of a tritium labelled form of a putative intermediate in monensin biosynthesis, in which the terminal carboxyl group is activated as a caprylcysteamine thiol ester.