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Paper | Regular issue | Vol 60, No. 7, 2003, pp.1573-1588
Published online, 28th April, 2003
DOI: 10.3987/COM-03-9764
Preparation of 6-Phenyl- and 8-Phenyl Tetrahydro-isoquinolines from Boldine

Wei-Jan Huang, Chung-Hsiung Chen, and Shoei-Sheng Lee*

*School of Pharmacy, College of Medicine, National Taiwan University, 1 Jen-Ai Rd. Sec. 1, Taipei, 100, Taiwan, R.O.C.


Four 6-phenyl- and 8-phenyltetrahydroisoquinolines were prepared by structural modifications of boldine nucleus. These involved four major reaction steps, including solvolysis of 2-hydroxyaporphine, ozonolysis of the C-9,10 double bond of phenanthrene nucleus leading to the key intermediate, and final Pictet-Spengler cyclization to respective target products.