96247-02-8

Upstream product

• 86782-19-6 (2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 
• 175979-30-3 Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester 
• 130021-74-8 (1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 
• 98-88-4 benzoyl chloride 
• 174966-55-3 (1R,2S,3S,4R,5R)-3-O-tert-butyldimethylsilyl-1-benzoyloxymethyl-4,5-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentaol 
• 174966-54-2 (1R,2R,3S)-3-O-tert-butyldimethylsilyl-5-benzoyloxymethyl-1,2-O-cyclohexylidene-4-cyclohexen-1,2,3-triol 
• 203317-83-3 (1R,2R,3S,4R)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidene-5-cyclohexene-1,2,3,4-tetrol 
• 175979-28-9 (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 175979-29-0 Benzoic acid (3R,4R,5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-cyclohex-1-enylmethyl ester 
• 203317-81-1 (1R,2R,3S)-5-(benzoyloxymethyl)-1,2-O-cyclohexylidene-4-cyclohexene-1,2,3-triol 
• 131221-89-1 (1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol 

Downstream Products

• 86702-29-6 (2R)-trans-2-acetoxy-3-(benzoyloxy)-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene 
• 175979-32-5 Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 176198-55-3 Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester 
• 176198-57-5 Benzoic acid (1S,2S,4S,5S,6R,7S)-5-acetoxy-6-hydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 74081-48-4 (1R-(1α,2α,4α,5β,6α,7α))-4-[(benzoyloxy)methyl]-3,8-dioxatricyclo[5,1,0,0^2,4]octane-5,6-diyl diacetate 
• 203457-70-9 Benzoic acid (1S,2S,3R,6S)-2-acetoxy-3-hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-1-ylmethyl ester 
• 203457-68-5 Benzoic acid (1R,2S,3R,6R)-2-acetoxy-3-hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-1-ylmethyl ester 
• 175979-34-7 4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octane-5,6-diol 5-acetate 
• 113467-93-9 (+)-boesenboxide 
• 58072-91-6 (+)-crotepoxide 
• 86702-28-5 tingtanoxide 
• 86702-28-5 Pipoxide acetate 
• 17550-38-8 α-senepoxide 
• 86747-02-6 (+)-β-senepoxide 

Relevant academic research and scientific papers

Enantiospecific syntheses of (+)-crotepoxide, (+)-boesenoxide, (+)-β- senepoxide, (+)-pipoxide acetate, (-)-iso-crotepoxide, (-)-senepoxide, and (- )-tingtanoxide from (-)-quinic acid

A convenient strategy that is ideally suited for the Construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield: Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

First enantiospecific syntheses of crotepoxide and iso-crotepoxide from (-)-quinic acid

The optically active crotepoxide 1 and iso-crotepoxide 2 have been constructed from quinic acid involving a singlet oxygen photooxygenation as the key step.

Total Synthesis of (+)-Pipoxide and (+)-β-Senepoxide and Their Diene Precursors

(2R)-trans-2,3-Diacetoxy-1-cyclohexa-4,6-diene (6), a diene precursor in the biosynthesis of highly oxygenated cyclohexane epoxides, has first been totally synthesized from the bromo lactone 16 derived from (1S)-endo-7-oxabicyclo2.2.1