Photooxygenation of a Microbial Arene Oxidation Product and Regioselective Kornblum–DeLaMare Rearrangement: Total Synthesis of Zeylenols and Zeylenones | Zendy

Palframan Matthew J. | Zendy; KociokKöhn Gabriele | Zendy; Lewis Simon E. | Zendy

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Photooxygenation of a Microbial Arene Oxidation Product and Regioselective Kornblum–DeLaMare Rearrangement: Total Synthesis of Zeylenols and Zeylenones

Author(s) -

Palframan Matthew J.,

KociokKöhn Gabriele,

Lewis Simon E.

Publication year - 2012

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201104035

Subject(s) - regioselectivity , photooxygenation , total synthesis , enantioselective synthesis , chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , singlet oxygen , oxygen

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.

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