213833-81-9

Upstream product

• 213833-70-6 (3R,5R)-(5-isopropenyl-2,3-dimethylcyclohex-1-enyloxy)trimethylsilane 
• 213833-82-0 (+/-)-2-methoxyhexahydrofuro[2,3-b]furan 
• 100460-14-8 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol 
• 104223-37-2 hexahydro furo<2,3-b>furan-2-one 
• 254752-70-0 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)acetonitrile 
• 6485-40-1 (R)-Carvone 
• 254752-69-7 (+/-)-cis,trans-toluene-4-sulfonic acid (2-methoxytetrahydrofuran-3-yl)methyl ester 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 272766-99-1 (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethyl-5-cyclohexenone 
• 272767-20-1 (2R,3R,5S)-2-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-hydroxymethylene-5-isopropenyl-2,3-dimethylcyclohexane 
• 272766-70-8 (1S,3R,4R,6S)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-1-(3-oxo-butyl)-cyclohexanecarbonitrile 
• 272767-21-2 (1S,3R,4R,6R)-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-6-isopropenyl-3,4-dimethyl-2-oxo-cyclohexanecarbonitrile 
• 272767-27-8 (1S,3R,4R)-3-[(2R,3aS,6aR)-hexahydrofuro[2,3-b]furan-2-yl]-3,4-dimethyl-2-oxo-cyclohexanecarbonitrile 
• 272767-26-7 (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-6-hydroxymethylene-2,3-dimethylcyclohexanone 
• 272766-54-8 (2R,3R)-2-[(2R,3aS,6aR)-hexahydrofuro[b]furan-2-yl]-2,3-dimethylcyclohexanone 

Relevant academic research and scientific papers

Enantioselective synthesis of functionalised decalones by robinson annulation of substituted cyclohexanones, derived from R-(-)-carvone

The copper catalysed conjugate addition of methyl magnesium iodide to cyclohexenones and trapping of the enolate as its trimethylsilyl enol ether, followed by a trityl hexachloroantimonate (TrSbCl6) catalysed Mukaiyama- reaction, was applied to R-(-)-carvone. This proved to be an efficient method for the preparation of C-2, C-3 functionalised chiral cyclohexanones. These compounds were converted into their α-cyano ketones, which were submitted to Robinson annulation reactions with methyl vinyl ketone. The scope and limitations of these annulations were investigated. A series of highly functionalised chiral decalones were obtained that can be used as starting compounds in the total syntheses of enantiomerically pure clerodanes. (C) 2000 Elsevier Science Ltd.

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