First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine
[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,...
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| Published in | Tetrahedron letters Vol. 60; no. 22; pp. 1471 - 1475 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
30.05.2019
Elsevier |
| Subjects | |
| Online Access | Get full text |
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| Abstract | [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. |
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| AbstractList | [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. The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtio-sulawesine was accomplished. The key intermediates, variously substituted 1-formyl-beta-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. (C) 2019 Elsevier Ltd. All rights reserved. |
| Author | Volk, Balázs Simig, Gyula Milen, Mátyás Szabó, Tímea Hazai, Viktor |
| Author_xml | – sequence: 1 givenname: Tímea surname: Szabó fullname: Szabó, Tímea – sequence: 2 givenname: Viktor surname: Hazai fullname: Hazai, Viktor – sequence: 3 givenname: Balázs surname: Volk fullname: Volk, Balázs – sequence: 4 givenname: Gyula surname: Simig fullname: Simig, Gyula – sequence: 5 givenname: Mátyás surname: Milen fullname: Milen, Mátyás email: milen.matyas@egis.hu |
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| Keywords | Alkaloids β-Carbolines Indole Total synthesis DESIGN ANALOGS beta-Carbolines NATURAL-PRODUCTS BIOLOGICAL EVALUATION ANTIMALARIAL DERIVATIVES |
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•First reported synthesis of trigonostemine A and trigonostemine B.•New synthesis of pityriacitrin and hyrtiosulawesine.•An improved... The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtio-sulawesine was accomplished. The key intermediates,... |
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| SubjectTerms | Alkaloids Chemistry Chemistry, Organic Indole Physical Sciences Science & Technology Total synthesis β-Carbolines |
| Title | First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine |
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