398478-56-3

Upstream product

• 398478-24-5 p-toluenesulfonic acid (2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptyl ester 
• 398478-23-4 (2R,3R,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-3-methoxymethoxy-2-(prop-2-enyl)heptan-1-ol 
• 398478-22-3 4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-hexane-1,2-diol 
• 398478-52-9 (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanal 
• 380909-41-1 (S)-tert-butyl((1-((4-methoxybenzyl)oxy)hex-5-en-3-yl)oxy)dimethylsilane 
• 380909-94-4 (3S)-1-[(4-methoxyphenyl)methoxy]hex-5-en-3-ol 
• 74035-91-9 (4S,5S)-5-(iodomethyl)-4-methyldihydrofuran-2(3H)-one 
• 943153-84-2 (3S,4R)-1-(tert-butyldiphenylsiloxy)-3-methyl-8-(tetrahydro-2H-pyran-2-yloxy)oct-6-yn-4-ol 
• 943153-83-1 methyl (3S,4R)-4-hydroxy-3-methyl-8-(tetrahydro-2H-pyran-2-yloxy)oct-6-ynoate 
• 84071-61-4 methyl (3S)-3-[(2S)-oxiran-2-yl]butanoate 
• 943153-89-7 (3S,4R)-4-(methoxymethoxy)-5-[(4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-3-methylpentan-1-ol 
• 943153-88-6 (3S,4R)-1-(tert-butyldiphenylsiloxy)-4-(methoxymethoxy)-5-[(4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-3-methylpentane 
• 943153-87-5 (3R,5R,6S)-8-(tert-butyldiphenylsiloxy)-5-(methoxymethoxy)-6-methyloctane-1,3-diol 
• 943153-86-4 {(2S,3S)-3-[(2R,3S)-5-(tert-butyldiphenylsiloxy)-2-(methoxymethoxy)-3-methylpentyl]oxiran-2-yl}methanol 

Downstream Products

• 1107631-32-2 3-fluoro-2-methoxy-6-(2-propenyl)-benzoic acid (1S,3R,4S)-3-(methoxymethoxy)-1-[2-[(4-methoxyphenyl)methoxy]ethyl]-4-methyl-6-heptenyl ester 
• 398478-72-3 (12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one 
• 398478-73-4 (12E)-(7S,9R,10S)-9-benzoyloxy-4-(tert-butyldimethylsilyloxy)-7-[(2E)-3-(carboallyloxy)prop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one 
• 398478-37-0 (12E)-(7S,9R,10S)-7-[(2E)-4-azido-4-oxo-but-2-enyl]-9-benzoyloxy-4-(tert-butyldimethylsilyloxy)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one 
• 398478-34-7 (12E)-(7S,9R,10S)-7-[(2E)-4-azido-4-oxo-but-2-enyl]-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one 
• 398478-33-6 (12E)-(7S,9R,10S)-4-benzoyloxy-9-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxabenzocyclodecen-5-one 
• 398478-36-9 (12E)-(7S,9R,10S)-9-benzoyloxy-4-(tert-butyldimethylsilyloxy)-7-[(2E)-3-carboxyprop-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclodecen-5-one 
• 198482-00-7 (2Z,4E)-Hepta-2,4-dienoic acid [(E)-3-((E)-(7S,9R,10S)-4,9-dihydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-propenyl]-amide 
• 198481-99-1 (-)-salicylihalamide A 
• 398478-58-5 (3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one 
• 320573-70-4 (3S,5R,6S,Z)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one 
• 398478-57-4 2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyloxy)ethyl]-3-methoxymethoxy-4-methylhept-6-enyl ester 
• 420794-28-1 (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-yl 2-allyl-6-(methoxymethoxy)benzoate 

Relevant academic research and scientific papers

Stereoselective synthesis of the macrocyclic core of (-)-salicylihalamides A and B

Stereoselective synthesis of the macrocyclic core of salicylihalamides A and B is described. The synthetic strategy features stereoselective iodolactonization, Sharpless asymmetric epoxidation, Mitsunobu esterification, and ring-closing metathesis. Georg

Total synthesis and initial structure - Function analysis of the potent V-ATPase inhibitors salicylihalamide A and related compounds

Salicylihalamide A is the first member of a growing class of macrocyclic salicylate natural products that induce a variety of interesting phenotypes in cultured mammalian cells. Salicylihalamide A was reported to be a unique and highly differential cytotoxin and a potent inhibitor of the mammalian vacuolar (H+)ATPase. The total synthesis of both enantiomers of salicylihalamide A, a revision of the absolute configuration assigned to the natural product, and extensive structure-function studies with synthetic salicylihalamide variants are reported. These studies were possible only due to a highly efficient synthetic strategy that features (1) a remarkably E-selective ring-closing olefin metathesis to construct the 12-membered benzolactone skeleton 29, (2) a mild stereocontrolled elaboration to E-alkenyl isocyanate 41, and (3) addition of carbon, oxygen, and sulfur nucleophiles to isocyanate 41 to obtain salicylihalamide A and congeners. We demonstrate for the first time that salicylihalamide A is a potent inhibitor of fully purified reconstituted V-ATPase from bovine brain, and have identified several similarly potent side chain modified derivatives, including salicylihalamide dimers 43-45. In combination, these studies have laid the foundation for ongoing studies aimed at a comprehensive understanding of salicylihalamide's mode-of-action, of potential relevance to the development of lead compounds for the treatment of osteoporosis and cancer.