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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.