159933-90-1

Basic information

• Product Name: palmarumycin CP(1)
• Synonyms: palmarumycin CP(1)
• CAS NO: 159933-90-1
• Molecular Formula: C₂₀H₁₂O₄
• Molecular Weight: 316.30688
• Mol File: 159933-90-1.mol

Chemical Properties

• Melting Point: 171-172 °C
• Boiling Point: 602.1°Cat760mmHg
• Flash Point: 226.8°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 4.3E-15mmHg at 25°C
• Refractive Index: 1.78
• PKA: 7.16±0.20(Predicted)
• CAS DataBase Reference: palmarumycin CP(1)(CAS DataBase Reference)
• NIST Chemistry Reference: palmarumycin CP(1)(159933-90-1)
• EPA Substance Registry System: palmarumycin CP(1)(159933-90-1)

Safety Data

• Hazardous Substances Data: 159933-90-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H12O4/c21-14-7-3-6-13-19(14)15(22)10-11-20(13)23-16-8-1-4-12-5-2-9-17(24-20)18(12)16/h1-11,21H

Upstream product

• 207504-83-4 5-Methoxyspiro<1,3>dioxin>-4-one 
• 207504-81-2 2,3-Dihydro-5-methoxyspiro<1,3>dioxin>-4-one 
• 207504-79-8 5-Methoxy-1,2,3,4-tetrahydrospiro<1,3>dioxine> 
• 33892-75-0 5-Methoxy-1-tetralone 
• 208346-34-3 C₂₄H₂₄O₅ 
• 208346-35-4 8-methoxy-5-(8'-methoxynaphthalene-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one 
• 208346-36-5 8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-3,4-dihydro-2H-naphthalen-1-one 
• 328005-54-5 5-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene-1-spiro-2'-dioxolane 
• 51062-77-2 5-hydroxy-8-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 5783-59-5 8-iodo-1-methoxy-naphthalene 
• 328005-52-3 C₂₀H₁₄O₄ 
• 208346-33-2 (+/-)-8-hydroxy-1-oxo-1,4,5,6,7,8-hexahydronaphthalene-4-spiro-2'-naphthol[1'',8''-de][1',3']dioxin 

Relevant articles and documents

Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals

Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors.

The synthesis of 1,8-dihydroxynaphthalene-derived natural products: Palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin a and novel analogues

Total syntheses of the title fungal metabolites are described via a route which utilises initial acetalisation with 1,8-dihydroxynaphthalene followed by elaboration of the ring A functionality. Novel analogues are also reported. Structural clarification is provided for palmarumycin CM, bipendensin and Sch 53,823.

Syntheses of palmarumycin CP1 and CP2, CJ-12,371 and novel analogues

Total syntheses of the title fungal metabolites are described via a route which utilises initial acetalisation with 1,8-dihydroxynaphthalene followed by elaboration of the ring A functionality. Novel analogues are also reported.

Total syntheses of palmarumycins CP1 and CP2 and CJ-12,371: Novel spiro-ketal fungal metabolites

Total syntheses of palmarumycins CP1 1 and CP2 9 and the structurally related CJ-12,371 11 are reported, thereby establishing a strategy for the synthesis of further natural products in the palmarumycins, diepoxines and preussomerines family.

Total synthesis of Palmarumycin BGs, C1 and Guignardin e

The first total synthesis of Palmarumycin BG1-3, BG5-6, C1 and Guignardin E (1-7) were achieved by the same intermediate Palmarumycin C2 through a N-benzyl cinchoninium chloride-catalyzed epoxidation, an organoselenium-mediated reduction, and a cerium(iii) chloride hydrate-promoted regioselective ring-opening and elimination of cyclic α,β-epoxy ketone as the key steps via6-7 step routes using 1,8-dihydroxynaphthalene (DHN) and 5-methoxytetralone as the starting materials in overall yields of 1.0-17.4%, respectively. Their structures and absolute configurations were characterized and determined by 1H, 13C NMR, IR, HR-ESI-MS and X-ray diffraction data. These compounds displayed significant inhibition activities against HCT116, U87-MG, HepG2, BGC823 and PC9 cell lines.

Flexible route to palmarumycin CP1and CP2and CJ-12.371 methyl ether

The total synthesis of palmarumycin CP1 (4) and CP2 (5) and racemic CJ-12.371 methyl ether (17) is described using the Diels-Alder reaction of benzoquinone 1,8-dihydroxynaphthalene acetal (10) with l-methoxy-1,3-butadiene under neat

Unified route to the palmarumycin and preussomerin natural products. Enantioselective synthesis of (-)-preussomerin G

The total syntheses of eight members of the palmarumycin family have been achieved, with identification of the absolute stereochemistry for three of these natural products. In addition, the ras-farnesyl transferase inhibitor (-)-preussomerin G has been synthesized, achieving the first enantioselective route for accessing this family of natural products. Highlights of the synthetic work include an asymmetric epoxidation of a cyclic enone in excellent yield and enantiomeric excess and a potentially biomimetic oxidative spirocyclization for the introduction of the bis-spiroketal array unique to the preussomerin natural products.