26457-63-6

Upstream product

• 25073-26-1 (E)-pent-2-ene-1,5-diol 
• 201230-82-2 carbon monoxide 
• 29293-07-0 pent-2-ene-1,5-diol 
• 100460-14-8 (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol 
• 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 
• 67-56-1 methanol 
• 104223-37-2 hexahydro furo<2,3-b>furan-2-one 
• 74915-94-9 1-(tert-butyldimethylsiloxy)-3-methyl-3-butene 
• 40760-35-8 3-methylenepentane-1,5-diol 
• 123703-38-8 4-[(tert-butyldimethylsilyl)oxy]-2-[2-[(tert-butyldimethylsilyl)oxy]ethyl]butanenitrile 
• 123703-39-9 4-[(tert-butyldimethylsilyl)oxy]-2-{2-[(tert-butyldimethylsilyl)oxy]ethyl}butanal 

Relevant academic research and scientific papers

Synthesis of perhydrofuro[2,3-b]furans from isopentenyl alcohol through carbonyl-ene and wacker-type reactions

A range of 2-substituted perhydrofuro[2,3-b]furans have been synthesized in a stereoselective manner through a sequence involving the Lewis-acid catalyzed carbonyl-ene reaction of a protected isopentenyl alcohol with a variety of enophiles, deprotection of the corresponding monoprotected diols, and palladium-catalyzed intramolecular acetalization under Wacker-type reaction conditions. A new synthetic approach toward the synthesis of perhydrofuro[2,3-b]furans is described. The strategy is based on the carbonyl-ene reaction for a protected isopentenyl alcohol with several activated enophiles followed by deprotection and palladium-catalyzed intramolecular acetalization. Copyright

Synthesis of Furo[2,3b]furans and Furo[2,36]pyrans via rhodium-catalyzed tandem hydroformylation/acetalization

Chemical equation presented Rhodium-catalyzed tandem hydroformylation/acetalization of α,ω-alkenediols gives facile access to perhydrofuro[2,3b]furans and perhydrofuro-[2,3b]pyrans in good yields. Similarly, benzoannelated tetrahydrofuro[2,3b]furans are o

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.