274263-03-5

Upstream product

• 91632-72-3 4,5,6,7-tetrahydroisobenzofuran 
• 129272-02-2 4,5,6,7-tetrahydroisobenzofuran-5-ol 
• 274263-07-9 Methanesulfonic acid (1R,3R,3aS,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester 
• 274263-01-3 ((1R,3R,3aS,4S,4aR,8aS,9aR)-1-Methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-methanol 
• 274262-97-4 (3R,3aR,4S,4aR,8aS,9aR)-4-Hydroxy-3-methyl-decahydro-naphtho[2,3-c]furan-1-one 
• 274262-93-0 C₁₃H₁₆O₃ 
• 274263-00-2 (1R,3R,3aR,4aR,8aS,9aR)-1-methoxy-3-methyl-4-methylenedodecahydronaphtho[2,3-c]furan 
• 274262-98-5 (1R,3R,3aR,4S,4aR,8aS,9aR)-1-Methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-ol 
• 274262-95-2 (3R,3aR,4S,4aR,8aR)-4-Hydroxy-3-methyl-3a,4,4a,5,6,7,8,8a-octahydro-3H-naphtho[2,3-c]furan-1-one 
• 274262-96-3 (3R,3aR,4S,4aR,9aR)-4-Hydroxy-3-methyl-3a,4,4a,5,6,7,8,9a-octahydro-3H-naphtho[2,3-c]furan-1-one 
• 274262-94-1 C₁₃H₁₈O₃ 
• 274262-99-6 (1R,3R,3aS,4aR,8aS,9aR)-1-methoxy-3-methyldecahydronaphtho[2,3-c]furan-4(1H)-one 
• 503443-60-5 4,5,6,7-tetrahydroisobenzofuran-5-yl methanesulfonate 
• 503443-47-8 4,5-dihydroisobenzofuran 

Downstream Products

• 503443-48-9 (2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels–Alder reaction: Total synthesis of (?)-himbacine

One-pot sequential reactions using the acyl moieties installed by enzymatic dynamic kinetic resolution of alcohols have been little investigated. In this work, the acryloyl moiety installed via the lipase/oxovanadium combo-catalyzed dynamic kinetic resolution of a racemic dienol [4-(cyclohex-1-en-1-yl)but-3-en-2-ol or 1-(cyclohex-1-en-1-yl)but-2-en-1-ol] with a (Z)-3-(phenylsulfonyl)acrylate underwent an intramolecular Diels–Alder reaction in a one-pot procedure to produce an optically active naphtho[2,3-c]furan-1(3H)-one derivative (98% ee). This method was successfully applied to the asymmetric total synthesis of (?)-himbacine.

Synthetic studies of himbacine, a potent antagonist of the muscarinic M2 subtype receptor 1. Stereoselective total synthesis and antagonistic activity of enantiomeric pairs of himbacine and (2′S,6′R)-diepihimbacine, 4-epihimbacine, and novel himbacine congeners

Total synthesis of an enantiomeric pair of himbacine 1 and ent-1 was achieved in a highly stereoselective manner by employing an intermolecular Diels-Alder reaction of tetrahydroisobenzofuran 8 with chiral furan-2(5H)-one (S)-9 and (R)-9, respectively, as a key step. An enantiomeric pair of (2′S,6′R)-diepihimbacine 24 and ent-24, 4-epihimbacine 4-epi-1, and novel himbacine congeners bearing the same tricyclic moiety as that of 1 were also successfully prepared by utilizing the key synthetic intermediates for 1, establishing the convergency and flexibility of the explored synthetic route. All of the synthesized compounds used were subjected to muscarinic M2 subtype receptor binding affinity assay, disclosing novel aspects of the structure-activity relationships for 1.