70518-33-1

Upstream product

• 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 
• 77311-86-5 4β,5β-dimethyl-7α-(1'-methoxycarbonyl-1'-hydroxyethyl)octalin-9-en-3,8-dione 
• 55050-26-5 5β,6β-dimethyl-2,7-dioxo-Δ^(1(10))-octalin 
• 77311-89-8 3,3-ethylenedithioligularenolide 
• 20489-24-1 (+/-)-ligularenolide 
• 93778-89-3 9β-hydroxy-10βH-furoeremophilane 

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.

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 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.