5090-65-3

Upstream product

• 26620-71-3 4,5-di-epi-aristolochene 
• 113729-71-8 (4aR,5S,8aR)-3,4a,5-Trimethyl-4,4a,5,6,7,8,8a,9-octahydro-naphtho[2,3-b]thiophene 
• 113775-84-1 (4aR,8S,8aR)-8,8a-Dimethyl-octahydro-isochromen-3-one 
• 113729-67-2 (4aR,8S,8aR)-8,8a-Dimethyl-octahydro-isochromene-3-thione 
• 113729-68-3 ((1R,2S,6R)-1,2-Dimethyl-6-thiazol-5-ylmethyl-cyclohexyl)-methanol 
• 113729-69-4 (1R,2S,6R)-1,2-Dimethyl-6-thiazol-5-ylmethyl-cyclohexanecarbaldehyde 
• 113729-65-0 (4aR,5S,8aR)-3,4a,5-Trimethyl-5,6,7,8,8a,9-hexahydro-4aH-naphtho[2,3-b]thiophen-4-one 
• 113729-63-8 1-((1R,2S,6R)-1,2-Dimethyl-6-thiazol-5-ylmethyl-cyclohexyl)-but-2-yn-1-one 
• 113729-70-7 {(1R,2S,6R)-1,2-Dimethyl-6-[4-(toluene-4-sulfonyl)-thiazol-5-ylmethyl]-cyclohexyl}-methanol 
• 54868-40-5 Δ^9(10),11(12)-eremophilene 
• 10219-75-7 [1S-(1α,7α,8aα)]-1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthalene 
• 113729-75-2 Dithiocarbonic acid O-((1S,2S,4aR,8S,8aR)-2-isopropyl-8,8a-dimethyl-decahydro-naphthalen-1-yl) ester S-methyl ester 
• 113729-75-2 Dithiocarbonic acid O-((1S,2R,4aR,8S,8aR)-2-isopropyl-8,8a-dimethyl-decahydro-naphthalen-1-yl) ester S-methyl ester 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Relevant academic research and scientific papers

(-)-1(10),11-Eremophiladien-9β-ol from the liverwort Marchantia polymorpha ssp. aquatica

A new eremophilane-type sesquiterpenoid, (-)-1(10),11-eremophiladien- 9β-ol, was isolated from the liverwort Marchantia polymorpha ssp. aquatica. Structure elucidation was performed by means of spectroscopic methods and chemical conversion to known eremophilone. The configuration was proved by NOE measurements and comparison of the products obtained by dehydration and hydrogenation of the alcohol with the hydrogenation products of both enantiomers of eremophilene and valencene by enantioselective gas chromatography with cyclodextrin derivatives.

Efficient and general approach to eremophilanes using siloxyalkyne-alkene metathesis

An efficient skeletal reorganization of a terminal alkene armed with an appropriate siloxy alkyne fragment is a pivotal step in our novel and general strategy for the construction of a bicyclic core of eremophilanes with complete diastereocontrol and high synthetic efficiency. Our approach features three significant strategic elements. First, the enyne metathesis precursor is assembled via a highly endo-selective Diels-Alder reaction. Second, installation of the siloxy group at the alkyne terminus enables the regio-selective assembly of the ensuing enone fragment via intramolecular enyne cyclization. Third, the common enone precursor offers the necessary flexibility of accessing several natural products of the eremophilane family.

THIAZOLES IN ORGANIC SYNTHESIS. NOVEL SYNTHESES OF MENTHANES AND EREMOPHILANES

Acetylenic thiazoles of proper design have been shown to undergo an intramolecular Diels-Alder reaction leading to fused-ring thiophene derivatives.When appropriately substituted, these latter materials can be readily converted to terpenes of the menthane

STEREOSPECIFIC TOTAL SYNTHESES OF 7α- AND 7β-EREMOPHILANE-6-ONE AND 7α- AND 7β-EREMOPHILANE

The title compounds have been prepared in a highly efficient fashion by a synthetic route involving an intramolecular Diels-Alder reaction of an acetylenic thiazole followed by reductive modification of the resulting fused-ring thiophene.

Agarofuran-, Eudesmane-, and Eremophilane-Type Sesquiterpenoids from Alpinia japonica (THUNB.) MIQ.

Three new sesquiterpenoids, 3α,4α-oxidoagarofuran, 3β,4β-oxidoagarofuran and Δ9(10)-eremophilen-11-ol, as well as 10-epi-γ-eudesmol, 4α-hydroxydihydroagarofuran, α-agarofuran, dihydroagarofuran and β-eudesmol were isolated from the rhizome of Alpinia japonica.Their structures were determined by chemical and spectroscopic methods.It is interesting from a biogenetic point of view that Δ9(10)-eremophilen-11-ol, β-eudesmol and agarofurans which possess the 10-epimeric eudesmane carbon skeleton were all contained in the same plant.Keywords--Alpinia japonica; Zingiberaceae; sesquiterpene; 3α,4α-oxidoagarofuran; 3β,4β-oxidoagarofuran; Δ9(10)-eremophilen-11-ol; 10-epi-eudesmane-type; 13C-NMR; X-ray analysis