1450741-52-2

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 1450741-53-3 (3,5-bis((benzyloxy)methoxy)-4-bromophenyl)methanol 
• 1450741-54-4 3,5-bis((benzyloxy)methoxy)-4-bromobenzaldehyde 
• 1450741-55-5 3,5-bis((benzyloxy)methoxy)-4-bromo-1-(E)-prop-1-en-1-ylbenzene 
• 1450741-56-6 3,5-bis((benzyloxy)methoxy)-4-bromo-1-(Z)-prop-1-en-1-ylbenzene 
• 1450741-58-8 (S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide 
• 1450741-59-9 (S,E)-4-(2,6-bis((benzyloxy)methoxy)-4-(prop-1-en-1-yl)phenyl)-3-methylbutan-2-one 
• 1450741-60-2 (S)-4-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-3-methylbutan-2-one 
• 1450741-61-3 (S)-4-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)-3-iodophenyl)-3-methylbutan-2-one 
• 1450741-62-4 (S)-5,7-bis((benzyloxy)methoxy)-3-((S)-1-hydroxyethyl)-6-((S)-2-methyl-3-oxobutyl)isobenzofuran-1(3H)-one 
• 1450741-64-6 C₃₇H₅₀O₈Si₂ 
• 1450741-65-7 C₄₆H₅₈O₁₁Si 
• 1450741-63-5 (S)-5,7-bis((benzyloxy)methoxy)-6-((2S,5R,7S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyl-3-oxooctyl)-3-((S)-1-hydroxyethyl)isobenzofuran-1(3H)-one 
• 1610702-33-4 (2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((1S,2S)-1,2-dihydroxypropyl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)-oxy)-2-methyloctan-3-one 
• 1610702-32-3 (2S,5R,7S)-1-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2-methyloctan-3-one 

Relevant academic research and scientific papers

Total synthesis of virgatolide B

The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp3-sp2 Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.

Total synthesis of virgatolide b via exploitation of intramolecular hydrogen bonding

A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp3-sp2 Suzuki-Miyaura cross-coupling of a β-trifluoroboratoamide with an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction. Intramolecular hydrogen bonding governed the regioselectivity of the key spiroketalization step, affording the natural product as a single regioisomer.