Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.