190278-32-1

Basic information

• Product Name: 3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
• Synonyms: 3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
• CAS NO: 190278-32-1
• Molecular Weight: 769.851
• Mol File: 190278-32-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one(190278-32-1)
• EPA Substance Registry System: 3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one(190278-32-1)

Safety Data

• Hazardous Substances Data: 190278-32-1(Hazardous Substances Data)

Upstream product

• 243990-53-6 (4-(benzyloxy)-3-methoxyphenyl)boronic acid 
• 123438-48-2 6-(benzyloxy)-7-methoxy-1-methylisoquinoline 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 29973-94-2 6-(benzyloxy)-1-(4-(benzyloxy)-3-methoxybenzyl)-7-methoxyIsoquinoline 
• 79418-71-6 4-(benzyloxy)-2-hydroxy-5-methoxybenzaldehyde 
• 51061-83-7 2,4-dihydroxy-5-methoxybenzaldehyde 
• 29973-91-9 4-benzyloxy-3-methoxyphenylacetic acid 
• 1700-29-4 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile 
• 33688-50-5 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene 
• 1253736-31-0 ethyl 3-[4-(benzyloxy)-2-bromo-5-methoxyphenyl]-2-nitroacrylate 
• 33693-48-0 4-benzyloxy-3-methoxybenzyl alcohol 
• 621-59-0 isovanillin 

Downstream Products

• 656836-79-2 14-(4-hydroxy-3-methoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 115982-22-4 14-(3,4-dihydroxyphenyl)-2,3,11,12-tetrahydroxy-6H-chromeno[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 97614-65-8 lamellarin D 

Relevant articles and documents

An Expeditious Modular Hybrid Strategy for the Diversity-Oriented Synthesis of Lamellarins/Azalamellarins with Anticancer Cytotoxicity

A modular hybrid strategy has been developed for the diversity-oriented synthesis of lamellarins/azalamellarins. The common pentacyclic pyrrolodihydroisoquinoline lactone/lactam core was formed via the Michael addition/ring closure (Mi-RC) and the copper(I) thiophene-2-carboxylate (CuTC)-catalyzed C-O/C-N Ullmann coupling. Subsequent direct functionalization at C1, DDQ-mediated C5C6 oxidation, and global deprotection of all benzyl-type O- and N-protecting groups furnished the desired lamellarins/azalamellarins. The late-stage functionalization at C1 provided a handle to accommodate a wider scope of functional groups as they need to tolerate only the DDQ oxidation and global deprotection. Moreover, with the C1-H pyrrole as the late-stage common intermediate, it was also possible to divergently exploit not only its nucleophilic nature to react with some electrophilic species but also some transition-metal-catalyzed cross-coupling reactions (via the intermediacy of the C1-iodopyrrole) to incorporate diversity at this position. Overall, this strategy simplifies the preparation of lamellarins/azalamellarins; including the Mi-RC, these C1-structurally diverse analogues could be prepared efficiently in 6-7 steps from the easily accessed 1-acetoxymethyldihydroisoquinoline and β-nitrocinnamate. Some selected azalamellarins were evaluated for their inhibitory effect against HeLa cervical cancer cells. An acute induction of intrinsic apoptosis was detected and may lead to growth suppression of or cytotoxicity against cancer cells.

Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D

An efficient construction of phenyl-substituted coumarin-pyrrole-isoquinoline-fused pentacycle via base-promoted Grob-type coupling of 3-nitrocoumarin and papaverine in a sealed tube is reported. This reaction is further applied to the total synthesis of lamellarin H in three linear steps and lamellarin D in eight linear steps with overall yields of 31% and 14%, respectively.

Total syntheses of lamellarin D and H. The first synthesis of lamellarin-class marine alkaloids

Total syntheses of marine polyaromatic alkaloids, lamellarin D (1) and H (2), are described. The pentacyclic lamellarin ring system was constructed by N-ylide mediated pyrrole ring formation and subsequent lactonization of 4 obtained by an assembly of known benzylisoquinoline 5, benzoate 6 and ethyl bromoacetate.