4871-90-3

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InChI:InChI=1/C15H22O2/c1-9-5-4-6-11-7-13-12(8-15(9,11)3)10(2)14(16)17-13/h9,11,13H,4-8H2,1-3H3/t9-,11+,13-,15+/m0/s1

Upstream product

• 70451-35-3 2-((4aR,8S,8aR)-8,8a-Dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl)-propionic acid methyl ester 
• 135305-72-5 2-((4aR,8S,8aR)-8,8a-Dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl)-acrylic acid methyl ester 
• 4231-35-0 methyl(diethylamino)acetylene 
• 93778-89-3 9β-hydroxy-10βH-furoeremophilane 
• 34335-94-9 Furanofukinol 
• 54911-14-7 6-O-Angeloylfuranokinol 
• 70492-93-2 3β(ax)-Hydroxyeremophilenolide 
• 70492-95-4 3-Oxoeremophilenolide 
• 77311-86-5 4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-3,8-dione 
• 55050-23-2 3,3-ethylenedioxy-4β,5β-dimethyloctalin-9-en-8-one 
• 77311-88-7 3,3-ethylenedithio-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 77311-80-9 3,3-ethylenedioxy-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 55050-26-5 5β,6β-dimethyl-2,7-dioxo-Δ^(1(10))-octalin 
• 77311-89-8 3,3-ethylenedithioligularenolide 

Relevant academic research and scientific papers

EREMOPHILENOLIDES FROM PETASITES JAPONICUS

Key Word Index - Petasites japonicus; Compositae; Senecioneae; sesquiterpene lactones; eremophilenolides; 13C NMR; CD spectra. - Chemical investigation of the young flower stalks of Petasites japonicus afforded some eremophilenolides, including a mixture of the two new compounds 6β-angeloyloxy-3β,8α-dihydroxyeremophil-7(11)-en-12,8β-olide and 6β-angeloyloxy-3β,8β-dihydroxyeremophil-7(11)-en-12,8α-olide.Their structures were elucidated by chemical and spectroscopic methods.The 13C NMR signals for the carbon atoms of the eremophilenolides were assigned with the help of Beierbeck's parameters.The CD spectra of the compounds are briefly discussed.

Acid-catalyzed rearrangement of 9-hydroxyfuranoeremophilanes to eremophilanlactones

9-Hydroxyfuranoeremophilanes 1-3 are the main components of freshly harvested rhizomes of P. hybridus (furanopetasin chemovar). They easily and quantitatively rearrange in the presence of traces of acid to give an epimeric mixture of 8-H-eremophilanlactones 4-6 (eremophilenolides). Besides subsequent oxidation, this is the most important reaction occurring during drying and storage of rhizomes of P. hybridus. A reasonable mechanism of the rearrangement is presented, and spectroscopic structure elucidation of 8-H-eremophilanlactones is discussed.

A new route to eremophilanes: synthesis of (±)-eremophilenolide, (±)-eremophiledinone, and (±)-deoxyeremopetasidione

A new and efficient route to the family of eremophilanes is reported. Key steps are the highly stereocontrolled Diels-Alder reaction and aldol condensation to furnish a cis-decalin system with the desired stereochemistry present in the eremophilane family of natural products. This approach is general and was utilized for the synthesis of (±)-eremophilenolide, (±)-eremophiledinone, and (±)-deoxyeremopetasidione.

The Photosensitized Oxygenation of Furanoeremophilanes. III. The Transformations to the Skeletally Isomeric Lactones from Furanofukinol

Pairs of the skeletal isomers of eremophilane-type lactones were synthesized from furanofukinol via photosensitized oxygenation, followed by lactone cleavage and refomation.Their stereochemistry has been clarified so as to be consistent with a classification method outlined in our earlier papers.

The Total Synthesis of (+)-Eremophilenolide

Naturally occuring (+)-Eremophilenolide was synthesized in 7percent overall yield from cyclohexenone (with optical yield of 89percent) The key step in the synthetic scheme was the enantiooselective alkylation of cyclohexenone followed by the construction of the cis A/B-ring system via butenylcyclohexenol annulation and of the 2-furanone unit via the α-epoxyketone - ynamine reaction.

A Total Synthesis of (+/-)-Eremophilenolide

(+/-)-Eremophilenolide was synthesized in 18percent overall yield from cyclohexanone.The A/B-ring system was prepared via butenylcyclohexenol-annulation and the 2-furanone unit via α-epoxyketone-ynamine reaction.