1329675-11-7

Upstream product

• 1401905-05-2 C₂₃H₃₀OSi 
• 68-12-2 N,N-dimethyl-formamide 
• 54340-72-6 ethyl (E)-2-heptenoate 
• 33467-76-4 (E)-hept-2-en-1-ol 
• 104528-17-8 (2R,3R)-(3-butyloxiranyl)methyl alcohol 
• 51703-66-3 (S)-(-)-1-heptyn-3-ol 
• 110-62-3 pentanal 
• 1329675-10-6 (4S)-4-(tert-butyldiphenylsilyloxy)oct-2-yn-1-ol 
• 1329675-09-3 tert-butyldiphenyl[(4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-yloxy]silane 
• 1329675-08-2 (4S)-1-(tetrahydro-2H-pyran-2-yloxy)oct-2-yn-4-ol 

Downstream Products

• 1329675-16-2 C₃₆H₄₅NO₃S₂Si 
• 1329675-14-0 (Z,3R,6S)-1-[(4S)-4-benzyl-2-thioxothiazolidin-3-yl]-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)dec-4-en-1-one 
• 1329675-15-1 methyl (2Z,5R,6Z,8S)-8-(tert-butyldiphenylsilyloxy)-5-(methoxymethoxy)dodeca-2,6-dienoate 
• 1329675-12-8 (2S,4Z)-4-{[(tert-butyl)diphenylsilyl]oxy}oct-2-enal 
• 1401904-89-9 (tert-butyl){[(1S,2Z)-1-butyl-3-[(2S)-oxiran-2-yl]prop-2-en-1-yl]oxy}diphenylsilane 

Relevant academic research and scientific papers

Total synthesis of umuravumbolide

A simple and efficient stereoselective total synthesis of (+)-umuravumbolide (1b) and (-)-deacetylumuravumbolide (1a) starting from commercially available pentanal is described. The synthesis involves Sharpless asymmetric epoxidation, Jacobsen's hydrolytic kinetic resolution (HKR), and the Yamaguchi oxirane opening as key steps (Scheme2).

Stereoselective total synthesis of umuravumbolide

A simple and efficient stereoselective total synthesis of desacetylumuravumbolide (1a) and umuravumbolide (1b), starting from commercially available valeraldehyde has been described. The synthetic strategy involves a highly enantioselective zinc-mediated addition of protected 2 alkyn-1-ol to aldehyde, a Crimmins aldol reaction, and Horner-Wadsworth-Emmons olefination as key steps. A simple and efficient stereoselective total synthesis of umuravumbolide and desacetylumuravumbolide starting from commercially available valeraldehyde is described. The synthetic strategy involves a highly enantioselective zinc-mediated addition, a Crimmins aldol reaction, and Horner-Wadsworth-Emmons olefination as key steps.