56495-98-8

Upstream product

• 56496-01-6 6-ethyl-5-hydroxy-7-methoxynaphthoquinone 
• 203579-21-9 (RS)-7-ethyl-4-hydroxy-6,8-dimethoxy-3,4-dihydro-1(2H)-naphthalenone 
• 150-19-6 O-methylresorcine 
• 78025-99-7 3,5-dimethoxy-4-ethylbenzaldehyde 
• 203579-18-4 4-ethyl-3,5-dimethoxybenzyl alcohol 
• 127-09-3 sodium acetate 
• 59276-37-8 3,4,5-trimethoxybenzaldehyde dimethyl acetal 
• 203579-19-5 6-ethyl-5,7-dimethoxy-3H-isobenzofuran-1-one 
• 616892-36-5 2,2-dimethyl-propionic acid 6-formyl-5-hydroxy-7-methoxy-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 616892-31-0 dithiocarbonic acid ethyl ester [2-(2-hydroxy-4-methoxy-phenyl)-2-oxo-ethyl] ester 
• 60965-24-4 2-bromo-1-(2-hydroxy-4-methoxy-phenyl)-ethanone 
• 203579-20-8 7-Ethyl-4-hydroxy-6,8-dimethoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid butyl ester 
• 616892-34-3 2,2-dimethyl-propionic acid 5-hydroxy-7-methoxy-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 616892-37-6 2,2-dimethyl-propionic acid 5-hydroxy-7-methoxy-6-vinyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 

Relevant academic research and scientific papers

13C and 2H N.M.R. Studies on the Biosynthesis of O-Methylasparvenone, a Hexaketide Metabolite of Aspergillus parvulus

Incorporations of singly and doubly labelled 13C acetates and acetate into O-methylasparvenone, a dihydronaphthalene metabolite of Aspergillus parvulus, and analysis of the resultant enriched samples by highfield 13C and 2H n.m.r. spectroscopy indicate a hexaketide biosynthesis and a novel acetate assembly pattern; the 2H-labelling pattern and levels of enrichment provide information on the sequence and mechanisms of the reduction, oxidation, and deoxygenation steps on the biosynthetic pathway.

Asymmetric total synthesis of (+)-: O -methylasparvenone, a rare nitrogen-free serotonin 2C receptor antagonist

The first enantioselective synthesis of the fungal metabolite (+)-O-methylasparvenone was achieved in eight steps and 22% overall yield from inexpensive 3,4,5-trimethoxybenzaldehyde dimethyl acetal. Key steps include (i) early-stage asymmetric alkynylation of an aromatic aldehyde with a propiolate, (ii) intramolecular Friedel-Crafts acylation, and (iii) site-selective cleavage of an aryl methyl ether.

Total synthesis of 10-norparvulenone and of O-methylasparvenone using a xanthate-mediated free radical addition - Cyclization sequence

(Matrix presented) A short synthesis of (±)-10-norparvulenone and (±)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition - cyclization sequence for the construction of the α-tetr

O-Methylasparvenone, a Nitrogen-free Serotonin Antagonist

O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT2C ligands and found to be 5-HT2C antagonists.They represent the first nitrogen-free serotonin ligands.The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester.A short and efficient synthesis of rac-1 was developed.This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established.

Regiospecific α-Substitution of Crotonic Esters. Synthesis of Naturally Occurring Derivatives of 6-Ethyljuglone

Methyl β-methoxycrotonate is alkylated regiospecifically, through the anion, in the α-position.Enolsilylation of the resulting β,γ-unsaturated ester affords the corresponding 1,1,2,3-tetrasubstituted butadiene.Cycloaddition of the latter to the appropriate halogenated benzoquinone, followed by various transformations, provides the first recorded syntheses of several natural products derived from 6-ethyl-7-methoxyjuglone.