218443-82-4

Upstream product

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

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.