198482-00-7

Basic information

• Product Name: N-[3-[5(R),14-Dihydroxy-6(S)-methyl-1-oxo-3,4,5,6,7,10-hexahydro-1H-2-benzoxacyclododecin-3(S)-yl]-1(Z)-propenyl]-2(Z),4(Z)-heptadienamide
• Synonyms: Salicylihalamide B
• CAS NO: 198482-00-7
• Molecular Formula: C₂₆H₃₃NO₅
• Molecular Weight: 439.55661
• Mol File: 198482-00-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: N-[3-[5(R),14-Dihydroxy-6(S)-methyl-1-oxo-3,4,5,6,7,10-hexahydro-1H-2-benzoxacyclododecin-3(S)-yl]-1(Z)-propenyl]-2(Z),4(Z)-heptadienamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-[5(R),14-Dihydroxy-6(S)-methyl-1-oxo-3,4,5,6,7,10-hexahydro-1H-2-benzoxacyclododecin-3(S)-yl]-1(Z)-propenyl]-2(Z),4(Z)-heptadienamide(198482-00-7)
• EPA Substance Registry System: N-[3-[5(R),14-Dihydroxy-6(S)-methyl-1-oxo-3,4,5,6,7,10-hexahydro-1H-2-benzoxacyclododecin-3(S)-yl]-1(Z)-propenyl]-2(Z),4(Z)-heptadienamide(198482-00-7)

Safety Data

• Hazardous Substances Data: 198482-00-7(Hazardous Substances Data)

Upstream product

• 1576-95-0 cis-2-penten-1-ol 
• 1576-86-9 cis-2-penten-1-one 
• 350794-14-8 bis[teri-butyl(dimethyl)silyl]-salicylihalamide 
• 579-75-9 2-Methoxybenzoic acid 
• 83458-92-8 ((2R,3R)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol 
• 345319-65-5 (2Z,4Z)-hepta-2,4-dienoic acid amide 
• 1026455-24-2 (R)-6-(benzyloxy)-3-(4-(methoxybenzyl)oxy)hexanal 
• 507480-22-0 (E)-(7S,9R,10S)-9-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-7-(3-hydroxy-propyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one 

Relevant articles and documents

Design, synthesis, and biological evaluation of fluorinated analogues of salicylihalamide

Salicylihalamide A (SA), a benzolactone enamide compound, possesses potent cytotoxicity against human tumor cell lines. SA is a selective inhibitor of mammalian vacuolar type H+-ATPase (V-ATPase), and is distinct from previously known V-ATPase

Total synthesis of (-)-salicylihalamide A and related congeners

A concise, highly efficient total synthesis of (-)-salicylihalamide A (1), a novel marine sponge metabolite, has been achieved. Key features of the synthetic strategy include a highly E-selective ring-closing metathesis to construct the 12-membered salicylihalamide A macrocycle and a practical method for installation of the labile ene-hepta-(Z,Z)-dienamide side chain involving N-acylation of enecabarmate 5, the latter derived from the corresponding α,β-unsaturated carboxylic acid 28 via acyl azide formation and thermal Curtius rearrangement. Two structurally simplified analogs (3 and 4) were also prepared which displayed significant, but attenuated cell growth inhibitory activity against several human tumor cell lines.

Total synthesis of (-)-salicylihalamide.

A concise total synthesis of the potent cytotoxic marine natural products salicylihalamide A and B (la, b) is reported. Key steps of our approach were the asymmetric hydrogenation reactions of beta-keto esters 18 and 32 catalyzed by [((S)-BINAP)Ru-Cl2]2. NEt3 and the cyclization of the macrolide core by ring closing olefin metathesis (RCM) using the "second-generation" ruthenium carbene complex 24 as the catalyst which bears an imidazol-2-ylidene ligand. The EIZ ratio obtained in this macrocyclization reaction was determined by the protecting groups at the remote phenolic OH group of the cyclization precursor. The elaboration of the resulting cycloalkene 37 into the final target involved a CrCl2-mediated synthesis of vinyliodide 49 which, after deprotection, did undergo a copper-catalyzed cross-coupling process with the (Z,Z)-configurated carboxamide 42 to form the labile enamide moiety of 1. Compound 42 was derived from a palladium-catalyzed Negishi coupling between butynylzinc chloride and 3-iodoacrylate 39 followed by a Lindlar reduction of enyne 40 thus obtained and a final aminolysis of the ester group.