254752-95-9

Upstream product

• 6485-40-1 (R)-Carvone 
• 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 
• 213833-77-3 (2R,3R,5R)-2-[(2R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofluoro[2,3-b]furan-2-yl]-5-isopropenyl-2,3-dimethylcyclohexanone 
• 213833-82-0 (+/-)-2-methoxyhexahydrofuro[2,3-b]furan 
• 213833-70-6 (3R,5R)-(5-isopropenyl-2,3-dimethylcyclohex-1-enyloxy)trimethylsilane 
• 104223-37-2 hexahydro furo<2,3-b>furan-2-one 
• 100460-14-8 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol 
• 124-63-0 methanesulfonyl chloride 
• 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 

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.