213833-77-3

Upstream product

• 6485-40-1 (R)-Carvone 
• 100460-14-8 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol 
• 104223-37-2 hexahydro furo<2,3-b>furan-2-one 
• 254752-69-7 (+/-)-cis,trans-toluene-4-sulfonic acid (2-methoxytetrahydrofuran-3-yl)methyl ester 
• 254752-70-0 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)acetonitrile 
• 213833-70-6 (3R,5R)-(5-isopropenyl-2,3-dimethylcyclohex-1-enyloxy)trimethylsilane 
• 213833-82-0 (+/-)-2-methoxyhexahydrofuro[2,3-b]furan 

Downstream Products

• 254752-71-1 (1R,2S,3R,5R,2'S,3a'R,6a'S)-2-(hexahydrofuro[2,3-b]furan-2'-yl)-5-isopropenyl-2,3-dimethyl-1-cyclohexanol 
• 254752-76-6 (3S,4S,5R,2'S,3a'R,6a'S)-3-[3-([1,3]dioxolan-2-yl)propyl]-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohexanone 
• 254752-75-5 (4S,5R,2'S,3a'R,6a'S)-3-[3-([1,3]dioxolan-2-yl)propyl]-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone 
• 254752-95-9 Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester 
• 254752-73-3 (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone 
• 254752-92-6 (1R,2S,3R,2'S,3a'R,6a'S)-4-(4-(hexahydrofuro[2,3-b]furan-2'-yl)-2,3-dimethyl-5-oxocyclohexyl)butyraldehyde 
• 254752-93-7 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethylcyclohex-3-enone 
• 213833-79-5 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethyl-3-(phenylsulfanyl)cyclohex-2-enone 
• 213833-80-8 (4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone 
• 213833-78-4 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethylcyclohex-2-enone 

Relevant academic research and scientific papers

Total synthesis of dihydroclerodin from (R)-(-)-carvone

The first total synthesis of the natural enantiomer of the insect- antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3- b]furan moiety was introduced in an early stage of the synthesis: The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

Enantioselective synthesis of highly functionalised cyclohexanones starting from R-(-)-carvone

Copper (1) catalysed conjugate addition of methylmagnesium iodide to R- (-)-carvone and trapping the enolate as its trimethylsilyl enol ether, followed by a trityl perchlorate (TrClO4) catalysed Mukaiyama-aldol reaction, is an efficient method