911367-23-2

Upstream product

• 880766-50-7 (-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate 
• 18524-18-0 (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 4957-71-5 (+)-(2R,3R)-1,2-O-isopropylidene-4-pentyne-1,2,3-triol 
• 108341-87-3 (2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 
• 143788-59-4 (2R,3S)-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 
• 143706-60-9 (2R,3R)-3-O-acetyl-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 
• 289666-91-7 (2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 
• 289666-90-6 (+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol 
• 289666-86-0 (-)-(2R,3S,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-1,2,4-pentanetriol 
• 289666-88-2 (+)-(2R,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-pentol 
• 289666-87-1 (+)-(2S,3R,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 
• 289666-89-3 (-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate 

Relevant academic research and scientific papers

Convergent total synthesis of (+)-mycalamide A

The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.