85700-43-2

Basic information

• Product Name: clavulone II
• Synonyms: clavulone II;(4R,5E,7E,12S,14Z)-4,12-Bis(acetyloxy)-9-oxoprosta-5,7,10,14-tetren-1-oic acid methyl ester;Claviridenone c
• CAS NO: 85700-43-2
• Molecular Formula: C₂₅H₃₄O₇
• Molecular Weight: 446.53326
• Mol File: 85700-43-2.mol

Chemical Properties

• Boiling Point: 556.6°Cat760mmHg
• Flash Point: 236.2°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 1.99E-12mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: clavulone II(CAS DataBase Reference)
• NIST Chemistry Reference: clavulone II(85700-43-2)
• EPA Substance Registry System: clavulone II(85700-43-2)

Safety Data

• Hazardous Substances Data: 85700-43-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H34O7/c1-5-6-7-8-9-10-17-25(32-20(3)27)18-16-23(28)22(25)13-11-12-21(31-19(2)26)14-15-24(29)30-4/h9-13,16,18,21H,5-8,14-15,17H2,1-4H3/b10-9-,12-11+,22-13-/t21-,25?/m0/s1

Upstream product

• 109-67-1 1-penten 
• 108-24-7 acetic anhydride 
• 460990-21-0 (4R)-4-hydroxy-4-(3-iodo-2-propenyl)-2-cyclopenten-1-one 
• 18495-27-7 1-bromooct-2-yne 
• 85611-86-5 claviridenone-a 
• 90195-67-8 4-Hydroxy-4-((Z)-oct-2-enyl)-cyclopent-2-enone 
• 93292-91-2 (E)-(R)-4-Acetoxy-7-oxo-hept-5-enoic acid methyl ester 
• 89156-50-3 (E)-(R)-4-Acetoxy-7-[(S)-2-hydroxy-2-((Z)-oct-2-enyl)-5-oxo-cyclopent-3-en-(E)-ylidene]-hept-5-enoic acid methyl ester 
• 93292-98-9 (E)-(R)-4-Acetoxy-7-hydroxy-7-[(S)-2-hydroxy-2-((Z)-oct-2-enyl)-5-oxo-cyclopent-3-enyl]-hept-5-enoic acid methyl ester 
• 89156-50-3 12-O-Desacetylclavulone II 
• 85700-42-1 claviridenone-d 
• 85611-86-5 claviridenone-a 
• 98892-13-8 (1R,2S,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-((Z)-oct-2-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentanol 
• 93292-92-3 (-)-(1R,4S)-(1,4-dihydroxy-cyclopent-2-enyl)-acetic acid t-butyl ester 

Downstream Products

• 145437-77-0 4-Bromo-benzoic acid (1R,5S)-5-methoxymethoxy-3-((Z)-oct-2-enyl)-4-[(E)-3-((R)-5-oxo-tetrahydro-furan-2-yl)-prop-2-en-(Z)-ylidene]-cyclopent-2-enyl ester 
• 918153-34-1 methyl 4-acetoxy-5-oxopentanoate 
• 66-25-1 hexanal 
• 85611-86-5 claviridenone-d 
• 85611-86-5 claviridenone-c 
• 85611-86-5 clavulone III 
• 129414-11-5 (4S)-4-Acetoxy-5E-<(4R)-4-acetoxy-6-benzyloxycarbonyl-2E-hexenylidene>-4-(2Z-octenyl)-2-cyclopenten-1-one 
• 87654-93-1 Benzoic acid (E)-(R)-4-[(2R,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2-((Z)-oct-2-enyl)-cyclopent-(Z)-ylidene]-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-but-2-enyl ester 
• 87654-91-9 Benzoic acid (1S,3R)-3-acetoxy-2-[(E)-(R)-4-acetoxy-6-methoxycarbonyl-hex-2-en-(Z)-ylidene]-3-((Z)-oct-2-enyl)-cyclopentyl ester 
• 87654-90-8 Benzoic acid (1R,3R)-3-acetoxy-2-[(E)-(R)-4-acetoxy-6-methoxycarbonyl-hex-2-en-(Z)-ylidene]-3-((Z)-oct-2-enyl)-cyclopentyl ester 
• 89156-58-1 4-Nitro-benzoic acid (1R,3R)-2-[(E)-(R)-4,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-en-(Z)-ylidene]-3-(tert-butyl-dimethyl-silanyloxy)-1-((Z)-oct-2-enyl)-cyclopentyl ester 
• 89156-57-0 Benzoic acid (1R,3R)-2-[(E)-(R)-4,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-en-(Z)-ylidene]-3-(tert-butyl-dimethyl-silanyloxy)-1-((Z)-oct-2-enyl)-cyclopentyl ester 
• 87654-89-5 4-Methoxy-benzoic acid (1R,3R)-3-acetoxy-2-[(E)-(R)-4-acetoxy-6-methoxycarbonyl-hex-2-en-(Z)-ylidene]-3-((Z)-oct-2-enyl)-cyclopentyl ester 
• 122804-29-9 (4S)-2-<(4S)-4-acetoxy-6-carbomethoxyhexyl>-4-(p-bromobenzoyloxy)-3-octyl-2-cyclopenten-1-one 

Relevant articles and documents

Synthesis of Clavulones (Claviridenones) via [3 + 2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone

Synthesis of clavulones II (1) and III (2) (claviridenones c and b), antitumor marine prostanoids, has been achieved via [3 + 2] annulation using reaction of (β-(phenylthio)acryloyl)silane 5 with methyl ketone enolate 6 followed by installation of the α-side chain by aldol reaction.

Efficient solid-phase synthesis of clavulones via sequential coupling of α- and ω-chains

We describe an efficient solid-phase synthesis of clavulones via the sequential coupling of the α- and ω-chains, involving two separate carbon - carbon bond-forming steps. The tetrahydropyranyl linker survived these reaction conditions and was cleaved without decomposing the unstable cross-conjugated dienones. Our methodology has allowed us to prepare six clavulone derivatives that are varied within the α-chain.

NEW PROSTANOIDS FROM SOFT CORAL

Four new anti-tumor active prostanoids, named claviridenone-a (3), claviridenone-b (4), claviridenone-c (5), and claviridenone-d (6), as well as 20-acetoxy-claviridenone-b (7) and 20-acetoxy-claviridenone-c (8), have been isolated from the Okinawan soft c

SYNTHESIS OF CLAVULONES (CLAVIRIDENONES)

New marine eicosanoid clavulones (claviridenones) were synthesized from the Corey lactone and D-glutamic acid.

TOTAL SYNTHESIS OF CLAVULONES

Total synthesis of clavulones in naturally occurring form has been accomplished by the aldol coupling of the hydroxy-cyclopentenone 2 efficiently obtainable from 1,2-bis-trimethylsilyloxycyclopentene (4) by using 1,3-hydroxy transposition via the allylic methanesulfonate 11 and the α,β-unsaturated aldehyde 3.

TOTAL SYNTHESIS OF MARINE PROSTANOIDS CLAVULONES

An enantioselective and stereoselective synthesis of novel marine prostanoids clavulone II (1) and 12-O-desacetylclavulone II (2) has been accomplished.

FOUR NEW PROSTANOIDS: CLAVIRIDENONE-A, -B, -C, AND -D FROM THE OKINAWAN SOFT CORAL CLAVULARIA VIRIDIS

The structures of four new prostanoids named claviridenone-a, -b, -c, and -d, which were isolated from the Okinawan soft coral Clavularia viridis, were elucidated as 1, 2, 3, and 4, respectively.