Lamellarin D

Base Information

• Chemical Name: Lamellarin D
• CAS No.: 97614-65-8
• Molecular Formula: C28H21NO8
• Molecular Weight: 499.477
• UNII: YEF6XD93VE
• DSSTox Substance ID: DTXSID501031665
• Nikkaji Number: J838.361H
• Wikipedia: Lamellarin_D
• Wikidata: Q18344928
• Metabolomics Workbench ID: 133055
• ChEMBL ID: CHEMBL373114
• Mol file: 97614-65-8.mol

Synonyms:lamellarin D

Chemical Property of Lamellarin D

Chemical Property:

• PSA: 123.00000
• LogP: 5.16170
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 499.12671663
• Heavy Atom Count: 37
• Complexity: 843

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=C3C4=CC(=C(C=C4C=CN3C5=C2C6=CC(=C(C=C6OC5=O)O)OC)O)OC)O

Technology Process of Lamellarin D

There total 134 articles about Lamellarin D which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3,11-diisopropoxy-14-(4-isopropoxy-3-methoxyphenyl)-2,12-dimethoxy-6H-chromeno[4′,3′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one (660396-67-8) → lamellarin D (97614-65-8)

Guidance literature:

With boron trichloride; In n-heptane; dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2005.10.014

Reference yield: 99.0%

14-(4-acetoxy-3-methoxyphenyl)-3,11-diacetoxy-2,12-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one (97633-82-4) → lamellarin D (97614-65-8)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃;

DOI:10.1021/jo061810h

Reference yield: 91.0%

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) → lamellarin D (97614-65-8)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 8h; under 760.051 Torr;

DOI:10.1021/acs.joc.7b01061

upstream raw materials:

3,10-Bis-benzyloxy-13-(4-benzyloxy-3-methoxy-phenyl)-2,11-dimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one

methyl 2-(2,4-dihydroxy-5-methoxyphenyl)-8-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-9-methoxypyrrolo[2,1-a]isoquinoline-3-carboxylate

3,11-diisopropoxy-14-(4-isopropoxy-3-methoxyphenyl)-2,12-dimethoxy-6H-chromeno[4′,3′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one

14-(4-acetoxy-3-methoxyphenyl)-3,11-diacetoxy-2,12-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

Downstream raw materials:

14-(4-acetoxy-3-methoxyphenyl)-3,11-diacetoxy-2,12-dimethoxy-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

14-(3,4-dihydroxyphenyl)-2,3,11,12-tetrahydroxy-6H-chromeno[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one

6-tert-butoxycarbonylamino-hexanoic acid 10-(6-tert-butoxycarbonylamino-hexanoyloxy)-13-[4-(6-tert-butoxycarbonylamino-hexanoyloxy)-3-methoxy-phenyl]-2,11-dimethoxy-6-oxo-6H-5-oxa-6b-aza-dibenzo[a,i]fluoren-3-yl ester

C₃₄H₃₃NO₈

Refernces

Utility of polymer-supported reagents in the total synthesis of lamellarins

10.1021/jo050388m

The study focuses on the total synthesis of lamellarins, a group of marine natural products with significant biological activities, using polymer-supported reagents. The researchers utilized four solid-supported reagents in the multistep synthesis process. Key chemicals included Amberlyst A-26 Br3-, polymer bound pyridine hydrobromide perbromide (PVPHP), and Amberlyst A-26 NaCO3-, which were used for selective keto R-bromination of ortho-substituted acetophenone derivatives to produce monobromination products. These products were then used in condensation reactions with benzyldihydroisoquinoline, mediated by Amberlyst A-26 NaCO3-. The synthesized 2H-pyrrole carbonates underwent intramolecular Friedel-Crafts transacylation and lactonization to provide the lamellarin skeleton. Amberlyst-15 was also used to mediate lactonization reactions, effectively combining two separate steps into one transformation. The purpose of these chemicals was to facilitate selective and efficient synthetic pathways for lamellarins, which are important for establishing structure-activity relationships and investigating their mechanisms of action, particularly in the context of cancer cell lines and multidrug-resistance.