3484-43-3

Upstream product

• 53343-13-8 1-hydroxypropan-2-one tetrahydropyran ether 
• 3241-65-4 (+/-)-8a-methyl-5-methylene-octahydro-naphthalen-2(1H)-one 
• 1201-61-2 1,2,3,4,5,8-hexahydro-1-hydroxy-6-methoxynaphthalene 
• 105631-42-3 ((4'aS,5'R,8'aR)-8'a-Methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl)-methanol 
• 105631-40-1 (4'aR,5'S,8'S,8'aS)-8'a-Methyl-8'-methylsulfanylthiocarboxyoxy-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carboxylic acid methyl ester 
• 98466-48-9 (1S,4S,4aS,8aR)-4-Hydroxy-4a-methyl-6-oxo-decahydro-naphthalene-1-carboxylic acid methyl ester 
• 65128-92-9 methyl (1α,4aβ)-6-methoxy-4a-methyl-4-oxo-1,2,3,4,4a,7-hexahydro-1-naphthoate 
• 105631-39-8 (4'aS,5'R,8'R,8'aR)-8'-Hydroxy-8'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carboxylic acid methyl ester 
• 98466-47-8 (1S,4S,4aS)-4-Hydroxy-4a-methyl-6-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 105631-41-2 (4'aS,5'R,8'aR)-8'a-Methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carboxylic acid methyl ester 
• 105631-43-4 (4'aS,8'aR)-8'a-Methyl-5'-methylene-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene] 
• 74064-03-2 (3aR,4aS,8aR,9aS)-3,8a-Dimethyl-5-methylene-3-phenylsulfanyl-decahydro-naphtho[2,3-b]furan-2-one 
• 600151-49-3 6-methoxy-4a-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-one 
• 162657-45-6 6-methoxy-4a-methyl-1-(trimethylsilyloxy)-2,3,4,4a,5,8-hexahydronaphthalene 

Downstream Products

• 3241-66-5 4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one 
• 94204-13-4 9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one 
• 182426-37-5 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 182426-37-5 3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 182426-37-5 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 6466-81-5 3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydro-4H-naphtho[2,3-b]furan-2-one 

Relevant academic research and scientific papers

Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)- biepiasterolide

The biomimetic synthesis of the bisesquiterpene lactones (±)-biatractylolide 1 and (±)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

Sesquiterpene Metabolites of the Antarctic Gorgonian Dasystenella acanthina

The ethereal extract of the Antarctic gorgonian Dasystenella acanthina was found to contain three main nonpolar and relatively transient sesquiterpene metabolites (1-3), which were isolated and submitted to spectral analysis. Two of them were identified as the previously reported compounds trans-β-farnesene (1) and isofuranodiene (3), whereas the third metabolite, the furanoeudesmane 2, was unknown. The structure elucidation of this new sesquiterpene was solved mainly on the basis of its spectral properties and correlation with known compounds.

TOTAL SYNTHESIS OF (+/-)-ATRACTYLON AND (+/-)-LINDESTRENE

The total synthesis of the eudesmane furanosesquiterpenes (+/-)-atractylon (1) and (+/-)-lindestrene (2) is described.Both 1 and 2 were synthesized via the methyl xanthate intermediate (10).

An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon

An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphthofuran-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.