Synthesis of anti-tubercular marine alkaloids denigrins A and B

Milandip Karak; Tohru Oishi; Kohei Torikai

doi:10.1016/j.tetlet.2018.06.013

Synthesis of anti-tubercular marine alkaloids denigrins A and B

Milandip Karak, Tohru Oishi, Kohei Torikai

Organic and Biological Chemistry

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.

Original language	English
Pages (from-to)	2800-2803
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2018.06.013
Publication status	Published - Jul 18 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2018.06.013

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abstract = "The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.",

author = "Milandip Karak and Tohru Oishi and Kohei Torikai",

note = "Funding Information: M.K. thanks to the Takeda Science Foundation for a postdoctoral research fellowship. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

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AU - Oishi, Tohru

AU - Torikai, Kohei

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Y1 - 2018/7/18

N2 - The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.

AB - The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.

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Synthesis of anti-tubercular marine alkaloids denigrins A and B

Abstract

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