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Paper | Regular issue | Vol 48, No. 5, 1998, pp.949-959
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8128
Establishment of Efficient Hydroxylation at Angular Position of 4a-Aryl-trans-decahydroisoquinolines

Koji Kawai, Kuniaki Kawamura, and Hiroshi Nagase*

*Basic Research Laboratories, Toray Industries, Inc., 111, Tebiro, Kamakura, Kanagawa, 248, Japan

Abstract

Efficient hydroxylation method at angular 8a position of 4a-aryl-trans-decahydroisoquinolines was described. By utilizing the transformation process, syntheses of 2-methyl- and 2-cyclopropylmethyl-8a-hydroxy-4a-(3-methoxyphenyl)-6-oxo-trans-decahydroisoquinolines (13 and 17), the useful molecules as an opioid message substructure, were attained. The key step in this transformation was N-protection of enamine intermediate by 2,2,2-trichloroethoxycarbonyl chloride and subsequent epoxidation and hydride reduction.