Preparation of 6-phenyl- and 8-phenyl tetrahydroisoquinolines from boldine

Wei J. Huang, Chung Hsiung Chen, Shoei Sheng Lee

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1573-1588
Number of pages16
JournalHeterocycles
Volume60
Issue number7
Publication statusPublished - Jul 1 2003
Externally publishedYes

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Tetrahydroisoquinolines
Cyclization
phenanthrene
boldine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of 6-phenyl- and 8-phenyl tetrahydroisoquinolines from boldine. / Huang, Wei J.; Chen, Chung Hsiung; Lee, Shoei Sheng.

In: Heterocycles, Vol. 60, No. 7, 01.07.2003, p. 1573-1588.

Research output: Contribution to journalArticle

Huang, Wei J. ; Chen, Chung Hsiung ; Lee, Shoei Sheng. / Preparation of 6-phenyl- and 8-phenyl tetrahydroisoquinolines from boldine. In: Heterocycles. 2003 ; Vol. 60, No. 7. pp. 1573-1588.
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