First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine

• Published in: Tetrahedron letters Vol. 60; no. 22; pp. 1471 - 1475
• Main Authors: Szabó, Tímea, Hazai, Viktor, Volk, Balázs, Simig, Gyula, Milen, Mátyás
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.05.2019; Elsevier
• Subjects: Alkaloids; Chemistry; Chemistry, Organic; Indole; Physical Sciences; Science & Technology; Total synthesis; β-Carbolines; Alkaloids; β-Carbolines; Indole; Total synthesis; DESIGN; ANALOGS; beta-Carbolines; NATURAL-PRODUCTS; BIOLOGICAL EVALUATION; ANTIMALARIAL; DERIVATIVES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2019.04.044

[Display omitted] •First reported synthesis of trigonostemine A and trigonostemine B.•New synthesis of pityriacitrin and hyrtiosulawesine.•An improved preparation of 1-formyl-β-carboline building blocks. The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.