29395-64-0

Upstream product

• 20489-24-1 eremophil-1(10),7(11),8-trien-12,8-olide 
• 20489-24-1 (+/-)-ligularenolide 
• 77311-89-8 3,3-ethylenedithioligularenolide 
• 55050-26-5 5β,6β-dimethyl-2,7-dioxo-Δ^(1(10))-octalin 
• 77311-80-9 3,3-ethylenedioxy-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 77311-88-7 3,3-ethylenedithio-4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-8-one 
• 55050-23-2 3,3-ethylenedioxy-4β,5β-dimethyloctalin-9-en-8-one 
• 77311-86-5 4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-3,8-dione 
• 92574-17-9 8β-hydroxy-eremophil-7(11),9(10)-dien-12,8-olide 
• 130395-64-1 10β-hydroxy-8β-methoxyeremophilenolide 

Relevant academic research and scientific papers

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.

ABSOLUTE CONFIGURATION OF EREMOPHILENOLIDES FROM HERTIA CHEIRIFOLIA

The absolute configurations of 8α-methoxy-10β-hydroxyeremophilenolide and 8β,10β-dihydroeremophilenolide from Hertia cheirifolia were determined by transformation into (-)tetrahydroligularenolide.

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.