186417-88-9

Upstream product

• 78186-80-8 3,3-dimethyl-4-oxohex-1-ene 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 136320-64-4 (2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 

Downstream Products

• 218443-81-3 (3S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4,4-dimethyl-5-oxo-heptanal 
• 220889-46-3 (2S,3S,4R,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,4,6,6-tetramethyl-dec-9-en-5-one 
• 220889-44-1 (2S,3S,4R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-(4-methoxy-benzyloxy)-2,4,6,6-tetramethyl-dec-9-en-5-one 
• 186417-90-3 (2R,5S)-5-hydroxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one 
• 186417-93-6 (-)-(2R,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethyloct-7-en-3-one 
• 186417-89-0 (R)-4-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,2-dimethyl-3-oxo-pentanal 
• 186417-92-5 (+)-(2R)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-4,4-dimethylhex-5-en-3-one 
• 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

Synthesis of the C(1)-C(9) segment of the cytotoxic macrolides epothilon A and B

The C(1)-C(9) segment 3 of the macrolides epothilon A and B 1, two new cytotoxic natural products, has been synthesized in a direct manner. Key steps in the synthesis are a stereoselective aldol reaction of 6 and 7 and a Brown allylation of 9.

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.