1392302-29-2

Upstream product

• 1392302-18-9 (S)-5-(benzyloxy)hept-1-ene 
• 1392302-16-7 (S,E)-6-(benzyloxy)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)oct-2-en-1-one 
• 1392302-21-4 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)prop-2-en-1-ol 
• 1392302-19-0 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)prop-2-en-1-one 
• 1392302-28-1 (R)-3-(benzyloxy)hept-6-en-1-yl p-toluenesulfonate 
• 1309953-47-6 2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)benzaldehyde 

Relevant academic research and scientific papers

Total synthesis of curvulone B and a proposed structure for dothiorelone B; Determination of the configuration of curvulone B and structural revision of phomopsin A

The total synthesis of curvulone B was achieved, and its absolute configuration unambiguously established, as had been determined by TD-DFT ECD calculations on the computed solution conformers. Key features of the synthesis were an olefin cross-metathesis of an α,β-unsaturated ketone as a common key building block with (R)-6-triethylsilyloxyhept-1-ene, and an intramolecular oxy-Michael addition of the hydroxyl enone obtained therefrom. An intermolecular metathesis of the enone with (S)-5-benzyloxyhept-ene also enabled us to prepare a proposed structure for dothiorelone B, thus leading to the confirmation of the structural revision of phomopsin A, a novel nine-membered cyclic phenol ether.2012 Elsevier Ltd.