139750-84-8Relevant articles and documents
Chiral Acetylenic Sulfoxide in Enantioselective Synthesis of Tetrahydroisoquinoline and Tetrahydro-β-carboline Alkaloids. Total Synthesis of (R)-(+)-Carnegine and (R)-(+)-Tetrahydroharman
Lee, Albert W. M.,Chan, Wing Hong,Tao, Yi,Lee, Yu Kai
, p. 477 - 482 (2007/10/02)
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.