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Paper | Regular issue | Vol 48, No. 2, 1998, pp.267-283
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8023
Synthesis of trans-4a-Aryl-6-oxo-decahydroisoquinolines

Kuniaki Kawamura, Koji Kawai, Toru Miyamoto, Koji Ooshima, and Hiroshi Nagase*

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


General and short synthesis of trans-4a-aryl-6-oxodecahydroisoquinolines was described. In particular, the synthesis of 2-cyclopropylmethyl-4a-(3-hydroxyphenyl)-trans-6-oxodecahydroisoquinoline (12), one of the remarkably useful molecule as an opioid message structural part, was attained in only seven steps. The key step in this synthetic approach was 1,4-conjugate addition of aryl moiety to sterically hindered enones (2).