Chiral acetylenic sulfoxide in enantioselective synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids. Total synthesis of (R)-(+)-Carnegine and (R)-(+)-tetrahydroharman
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 477-481
- https://doi.org/10.1039/p19940000477
Abstract
Michael addition of 2-(3,4-dimethoxyphenyl)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)(+)-Carnegine and (R)-(+)-tetrahydroharman have been synthesized.Keywords
This publication has 15 references indexed in Scilit:
- Chiral acetylenic sulfoxide in alkaloid synthesis. Total synthesis of (R)-(+)-carnegine.Tetrahedron Letters, 1991
- Acetylenic sulphoxides in organic synthesis: Diels–Alder reactionsJournal of the Chemical Society, Chemical Communications, 1988
- Application of a modified Pictet–Spengler reaction to the synthesis of optically active tetrahydro-β-carbolines, key intermediates in the preparation of many indole alkaloidsJournal of the Chemical Society, Perkin Transactions 1, 1988
- Convenient synthesis of sulfinate esters from sulfonyl chloridesThe Journal of Organic Chemistry, 1987
- The formation of optically active 1,3-disubstituted and 1,1,3-trisubstituted tetrahydro-β-carbolines using a modified Pictet–Spengler reactionJournal of the Chemical Society, Chemical Communications, 1985
- Sulfoximine-mediated syntheses of optically active alcoholsThe Journal of Organic Chemistry, 1982
- New method for the methylation of aminesThe Journal of Organic Chemistry, 1972
- Configurational Relationships among Some Sulfoxides1The Journal of Organic Chemistry, 1964
- Synthesis of (+)-ethyl -tolyl sulfoxide from (−)-menthyl (−)--toluenrsulfinateTetrahedron Letters, 1962
- 246. Chemical correlation of the absolute configurations of salsolidine, salsoline, and calycotomine with the amino-acidsJournal of the Chemical Society, 1960