1379660-00-0

Upstream product

• 172877-75-7 (3aS,7aR)-methyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 172877-74-6 (-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid 
• 172877-76-8 ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 
• 32359-20-9 (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid 
• 1379659-99-0 C₂₃H₃₄O₆Si 
• 1379659-82-1 [(3aS,7aR)-2,2-dimethyl-7aH-benzo[1,3]dioxol-3a-yl]methyl benzoate 

Relevant academic research and scientific papers

Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLamare rearrangement: Total synthesis of zeylenols and zeylenones

We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (-)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum-DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product. New light on a Korny rearrangement: Biooxidation of benzoic acid with R. eutrophus B9 gives a dearomatised diene diol acid that allows concise access to the zeylenol and zeylenone family of polyoxygenated cyclohexene natural products. The synthesis employs diene photooxygenation and a new regioselective variant of the Kornblum-DeLaMare endoperoxide fragmentation has been developed (see scheme).