58072-91-6

Upstream product

• 108-24-7 acetic anhydride 
• 64011-11-6 Benzoic acid (1R,2R,4S,5S,6S,7R)-5,6-dihydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester 
• 74766-77-1 DL-di-O-acetyl-(1,3/2,4,6)-3,4-dibromo-6-benzoyloxymethyl-1,2-cyclohexanediol 
• 69982-70-3 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide 
• 74766-83-9 DL-1,2-di-O-acetyl-(1,4/2,3)-3,4-dibromo-6-bromomethyl-5-cyclohexene-1,2-diol 
• 74766-84-0 DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol 
• 74766-79-3 DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol 
• 74766-78-2 3,4-di-O-acetyl-1,5-anhydro-6-bromo-2,6-dideoxy-5a-carba-DL-arabino-hex-1-enitol 
• 532-32-1 sodium benzoate 
• 74766-86-2 DL-3,4-di-O-Acetyl-1,2-anhydro-(1,2,3/4)-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4-tetrol 
• 17550-38-8 DL-3,4-di-O-acetyl-1,2-anhydro-(1,2/3,4)-2C-(benzoyloxymethyl)-5-cyclohexene-1,2,3,4-tetrol 
• 74766-85-1 trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene 
• 57987-33-4 Benzoic acid 2-acetoxy-5-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 
• 57987-34-5 Benzoic acid 2-acetoxy-5-(tetrahydro-pyran-2-yloxy)-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 

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.

Conversion of β-Senepoxide to Crotepoxide: Total Synthesis of (+)-Crotepoxide

Total synthesis of (+)-crotepoxide has been accomplished by chemical conversion of (+)-β-senepoxide which was prepared from (-)-7-endo-oxabicyclohept-5-ene-2-carboxylic acid.

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE.

The title substituted 1,3-cyclohexadiene was prepared in three steps from the readily available DL-1,2-di-O-acetyl-(1,3/2)-3-bromomethyl-5-cyclohexene-1,2-diol. Epoxidation of it with m-chloroperoxybenzoic acid in 1,2-dichloroethane afforded several stere

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE

Epoxidation of a newly prepared trans-5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene by m-chloroperbenzoic acid in dichloroethane gave several isomeric compounds of the biologically important highly oxygenated cyclohexane derivatives.

STEREOSELECTIVE SYNTHESIS OF (+/-)-SENEPOXYDE AND (+/-)-CROTEPOXIDE

Stereoselective synthesis of (+/-)-senepoxyde and (+/-)-crotepoxyde is described starting from 2-hydroxymethyl-1,4-benzoquinone through the retro-Diels-Alder reaction.