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Paper | Regular issue | Vol 51, No. 10, 1999, pp.2343-2347
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8591
Synthesis of a Novel 7,14β-Ethano-bridged Opiate

Han Yu, Lijuan Wang, Judith L. Flippen-Anderson, Xinrong Tian, Andrew Coop, and Kenner C. Rice*

*Laboratory of Medicinal Chemistry, National Institute of Diabetes Digestive and Kidney Diseases, National Institute of Health, Bldg.8, Rm. B1-23 Betheda, MD 20892-0815, U.S.A.

Abstract

A novel 7, 14β-ethano-bridged opiate (1) was prepared from the known 14-alkenylcodeinone (3) in two steps. Selective reduction of the enone double bond of 3 followed by ozonolysis led to an aldehyde intermediate, which was cyclized in situ through an intramolecular aldol condensation to give the rigid hexacyclic derivative (1).