186417-90-3

Upstream product

• 106356-53-0 B-allyldiisopinocampheylborane 
• 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 
• 1730-25-2 allylmagnesium bromide 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 186417-88-9 (-)-(5R,6S,7S)-6-hydroxy-8-[(4-methoxybenzyl)oxy]-3,3,5,7-tetramethyloct-1-en-4-one 
• 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 
• 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 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 78186-80-8 3,3-dimethyl-4-oxohex-1-ene 

Downstream Products

• 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 
• 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 

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.

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.