77704-70-2

Upstream product

• 98-01-1 furfural 
• 139437-47-1 (R)-2-{[1-Furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-ethanol 
• 56613-80-0 D-2-phenylglycinol 
• 139437-47-1 (R)-2-{[1-Furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-ethanol 
• 132168-60-6 (-)-(R)-2<<(Furan-2-yl)methyl>amino>-2-phenylethanol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 132168-56-0 (-)-(R)-<2--N-(3-methylbut-2-enoyl)amino>-2-phenylethyl>-3-methyl-but-2-enoat 

Downstream Products

• 470690-42-7 (1R,5S,7S)-3-[(1R)-2-chloro-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one 
• 470690-17-6 (+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-23-4 (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-22-3 (+)-(1R,2S,4R,5S)-1-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-27-8 (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol 
• 470690-24-5 (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(1S)-3-oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-30-3 (-)-(S)-acetic acid [(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-hydroxymethylcyclohex-1-enyl)methyl ester 
• 470690-28-9 (-)-(S)-[(1R,2R,4R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl][2-(tert-butyldimethylsilyloxymethyl)cyclohex-1-enyl]methanol 
• 470690-29-0 (-)-(S)-acetic acid [(1R,2R,4R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl][2-(tert-butyldimethylsilyloxymethyl)cyclohex-1-enyl]methyl ester 
• 132168-57-1 (-)-(3aR,4R,5R,6R,7aS,1'R)-3a,6:4,5-Diepoxyperhydro-2-(2'-hydroxy-1'-phenylethyl)-7,7-dimethyl-1H-isoindol-1-on 
• 132168-58-2 (+)-(3aR,4R,5R,6R,7aS,1'R)-2-(1'-Cyclohexyl-2'-hydroxyethyl)-3a,6:4,5-diepoxyperhydro-7,7-dimethyl-1H-isoindol-1-on 
• 77704-41-7 (-)-(3aR,6S,7aS,1'R)-3a,6-Epoxyperhydro-2-(2'-hydroxy-1'-phenylethyl)-7,7-dimethyl-1H-isoindol-1-on 
• 77704-41-7 (1S,5S,7R)-3-((R)-2-Hydroxy-1-phenyl-ethyl)-6,6-dimethyl-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]decan-4-one 
• 122274-03-7 Toluene-4-sulfonic acid (1S,2R,4R)-1,3,3-trimethyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl ester 

Relevant academic research and scientific papers

Studies towards the total synthesis of solanoeclepin A: Synthesis of the 7-oxabicyclo[2.2.1]heptane moiety and attempted seven-membered ring formation

This paper details studies towards the total synthesis of solanoeclepin A (1), the most active natural hatching agent of potato cyst nematodes. The first goal was the preparation of the tetracyclic left-handed substructure 2 in enantiopure form. The 7-oxabicyclo[2.2.1]heptane moiety was obtained via a diastereoselective intramolecular Diels-Alder strategy by using (R)-phenylglycinol as a chiral auxiliary as pioneered by Mukaiyama. A chromium-mediated nickel-catalysed coupling of aldehyde 5 with vinyl triflate 6 gave α,β-unsaturated lactone 18 as a single stereoisomer. The seven-membered ring was expected to arise from a McMurry coupling of dialdehyde 4. Surprisingly, oxidation of diol 24 did not lead to the desired dialdehyde 4, but to the eight-membered ring lactone 25.

Enantioselectve synthesis of the tetracyclic left-hand substructure of solanoeclepin A

The synthesis of the enantiopure left-hand substructure of solanoeclepin A is described. Key steps include a chromium-mediated coupling of an oxabicyclic aldehyde with a β-ketoester-derived enol triflate to give a lactone, and a ring-closing metathesis reaction to form the seven-membered ring.

Carotenoids with 7-Oxabicycloheptyl End Groups. Synthesis of (2S,5R,6S,2'S,5'R,6'S)-2,5:2',5'-Diepoxy-5,6,5',6'-tetrahydro-β,β-carotene

Mukayama's ester 6 (methyl (1S,2R,5S)-2,5-epoxy-2,6,6-trimethylcyclohexane-1-carboxylate) was transformed in a few conventional steps into the title compound 14.Its CD curve was found to be significantly different from that of the analogous 3,6-epoxide, a