Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-carnegine and (R)-(+)-tetrahydroharman

Albert W M LEE*, Wing Hong CHAN, Yi Tao, Yu Kai Lee

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Michael addition of 2-(3,4-dirnethoxyphenyl)ethylamine 3 or tryptamine 4 onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded the basic alkaloid skeleton of tetraisoquinoline and tetrahydro-β-carboline in high to moderate diastereoselectivity. Optically pure (R)-(+)-carnegineand (R)-(+)-tetrahydroharman have been synthesized.

Original languageEnglish
Pages (from-to)477-481
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
DOIs
Publication statusPublished - 1994

Scopus Subject Areas

  • Chemistry(all)

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