30270-60-1

Basic information

• Product Name: MONOCERIN
• Synonyms: MONOCERIN;(2S)-2,3,3aα,9bα-Tetrahydro-6-hydroxy-7,8-dimethoxy-2β-propyl-5H-furo[3,2-c][2]benzopyran-5-one
• CAS NO: 30270-60-1
• Molecular Formula: C16H20O6
• Molecular Weight: 308.33
• Product Categories: Antibiotic
• Mol File: 30270-60-1.mol

Chemical Properties

• Boiling Point: 506.7 °C at 760 mmHg
• Flash Point: 187.5 °C
• Appearance: /
• Density: 1.235 g/cm³
• Vapor Pressure: 6.89E-11mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: MONOCERIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONOCERIN(30270-60-1)
• EPA Substance Registry System: MONOCERIN(30270-60-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 30270-60-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Colletotrichum species.

InChI:InChI=1/C16H20O6/c1-4-5-8-6-11-14(21-8)9-7-10(19-2)15(20-3)13(17)12(9)16(18)22-11/h7-8,11,14,17H,4-6H2,1-3H3/t8-,11+,14+/m0/s1

Upstream product

• 30270-61-2 (2S*,3aR*,9bR*)-2,3,3a,9b-tetrahydro-6,7,8-trimethoxy-2-propyl-5H-furol(3,2-c)⁽²⁾benzopyran-5-one 
• 2305-25-1 3-hydroxy-hexanoic acid ethyl ester 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 123731-52-2 3,4,5-trimethoxybenzyl phenyl sulfide 
• 3249-68-1 ethyl butyroyl acetate 
• 123731-54-4 (+/-)-3-t-butyldimethylsilyloxy-1-hexanol 
• 123731-56-6 (+/-)-3-t-butyldimethylsilyloxy-1-iodohexane 
• 123731-53-3 ethyl 3-((tert-butyldimethylsilyl)oxy)hexanoate 
• 123731-62-4 (+/-)-(E)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol 
• 123731-55-5 Toluene-4-sulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-hexyl ester 
• 123731-63-5 2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol 
• 123731-65-7 6-((2S,3R)-3-Hydroxy-5-propyl-tetrahydro-furan-2-yl)-2,3,4-trimethoxy-benzoic acid 
• 123731-61-3 (+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene 
• 123731-59-9 1-(2-bromo-3,4,5-trimethoxyphenyl)-4-t-butyldimethylsilyloxy-1-heptanol 

Relevant articles and documents

Enantioselective Total Synthesis of (+)-Monocerin, a Dihydroisocoumarin Derivative with Potent Antimalarial Properties

We describe here the enantioselective synthesis of (+)-monocerin and its acetate derivative. The present synthesis features an efficient optically active synthesis of the β-hydroxy-?-lactone derivative with high enantiomeric purity using Sharpless dihydroxylation as the key step. The synthesis also highlights a tandem Lewis acid-catalyzed, oxocarbenium ion-mediated diastereoselective syn-allylation reaction, and a methoxymethyl group promoted methylenation reaction. We investigated this reaction with a variety of Lewis acids. A selective CrO3-mediated oxidation of isochroman provided the corresponding lactone derivative. The synthesis is quite efficient and may be useful for the preparation of derivatives.

Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation

A concise stereoselective total synthesis of (+)-monocerin has been accomplished using cross metathesis, tandem dihydroxylation-SN2 cyclisation and intramolecular alkoxycarbonylation as key steps. Cross-metathesis of 2-iodo-3,4,5-trimethoxyvinylbenzene and (R)-hepten-4-ol, followed by tandem dihydroxylation-SN2 cyclisation generated a tri-substituted tetrahydrofuran ring. Finally, the dihydroisocoumarin was obtained by an intramolecular alkoxycarbonylation. In this paper, we have developed an expedient operationally simple Pd(OAc)2/bathocuproine catalysed alkoxycarbonylation under atmospheric pressure of carbon monoxide. The catalytic system developed here can be useful for the synthesis of various dihydroisocoumarins and phthalides.

Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation-lactonization approach

A simple and novel synthesis of (+)-monocerin was achieved in 15 steps and 15.5% overall yield from 3-buten-1-ol employing hydrolytic kinetic resolution, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclizat

Asymmetric total synthesis of fusarentin 6-methyl ether and its biomimetic transformation into fusarentin 6,7-dimethyl ether, 7-O-demethylmonocerin, and (+)-monocerin

A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues fusarentin 6,7-dimethyl ether (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones of 7-O-demethylmonocerin (3) and (+)-monocerin (4) were efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of fusarentin 6-methyl ether (1) using hypervalent iodine reagent.

Asymmetric total synthesis of (+)-monocerin

A concise asymmetric total synthesis of (+)-monocerin has been accomplished. The cis-fused furobenzopyranone of monocerin was efficiently constructed via a Lewis acid-mediated stereoselective cyclization of 1,2,4-triols intermediate.

Asymmetric synthesis of 4,8-dihydroxyisochroman-1-one polyketide metabolites using chiral hypervalent iodine(III)

Stereoselective oxylactonization of ortho-alkenylbenzoate with chiral hypervalent iodine is applied to the asymmetric synthesis of 4-oxyisochroman-1-one polyketide metabolites including 4-hydroxymellein (1), a derivative of fusarentin 2, monocerin (3), and an epimer of monocerin epi-3.

Radical cyclization of vinylic ethers: Expedient synthesis of (+)-monocerin

(Chemical Equation Presented) Stereoselective synthesis of (+)-monocerin was accomplished via radical cyclization of a vinylic ether intermediate.

A concise, convergent total synthesis of monocerin

A concise and convergent eight-step synthesis of the antifungal metabolite monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approac

SYNTHESIS OF MONOCERIN, AN ANTIFUNGAL, INSECTICIDAL AND PHYTOTOXIC HEPTAKETIDE METABOLITE OF EXSEROHILUM MONOCERAS

Both the naturally occurring enantiomer and the racemate of monocerin were synthesized for the first time.