Chemoenzymatic synthesis of the morphine skeleton via radical cyclization and a C 10C 11 closure

A short synthesis of a morphinan skeleton has been accomplished. The key steps involve enzymatic dihydroxylation of β-bromoethyl benzene, vinyl and aryl radical cyclizations, and Friedel-Crafts closure of an aziridinium ion or an acid-catalyzed closure of an aldehyde to form the C 10C 11 bond. Morp...

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Published inTetrahedron letters Vol. 37; no. 45; pp. 8155 - 8158
Main Authors Butora, Gabor, Hudlicky, Tomas, Fearnley, Stephen P., Gum, Andrew G., Stabile, Michele R., Abboud, Khalil
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.11.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OPIUM-ALKALOIDS
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Summary:A short synthesis of a morphinan skeleton has been accomplished. The key steps involve enzymatic dihydroxylation of β-bromoethyl benzene, vinyl and aryl radical cyclizations, and Friedel-Crafts closure of an aziridinium ion or an acid-catalyzed closure of an aldehyde to form the C 10C 11 bond. Morphinan 1 6 was synthesized from 2-(2-bromoethyl)-bromobenzene ( 6) in 13 steps.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01867-9