Collect. Czech. Chem. Commun. 2000, 65, 561-569

Comparison of Approaches to ent-Morphine via Radical, Cationic, and Heck-Type Cyclizations

Dean A. Frey, Caiming Duan, Ion Ghiviriga and Tomáš Hudlický*

Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


3-(2-{6S-(2-Bromo-6-methoxyphenoxy)-5S-[tert-butyl(dimethyl)silyloxy)cyclohex-1-en-1-yl}ethyl)oxazol-2(3H)-one 14 was subjected to Heck cyclization conditions to afford diben- zofuran derivative 16. The comparison of stepwise vs cascade approaches to 8 via radical, cationic, and Heck-type cyclizations is discussed.

Keywords: Morphine; Heck reaction; Alkaloids; Biooxidation; Total synthesis; Palladium; Cascade cyclizations.

References: 25 live references.