Total Synthesis of Keramaphidin B and Ingenamine by Base-Catalyzed Diels-Alder Reaction Using Dynamic Regioselective Crystallization

Yuki Kurihara; Minori Yagi; Takashi Noguchi; Haruka Yasufuku; Ayane Okita; Sho Yoshimura; Takeshi Oishi; Noritaka Chida; Toshitaka Okamura; Takaaki Sato

doi:10.1021/jacs.4c02338

Total Synthesis of Keramaphidin B and Ingenamine by Base-Catalyzed Diels-Alder Reaction Using Dynamic Regioselective Crystallization

Yuki Kurihara
, Minori Yagi
, Takashi Noguchi
, Haruka Yasufuku
, Ayane Okita
, Sho Yoshimura
, Takeshi Oishi
, Noritaka Chida
, Toshitaka Okamura
, Takaaki Sato

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

8 Citations (Scopus)

Abstract

The control of the selectivity is a central issue in the total synthesis of complex natural products. In this paper, we report the total synthesis of (±)-keramaphidin B and (±)-ingenamine. The key reaction is a DMAP-catalyzed Diels-Alder reaction in which the regioselectivity is completely controlled by dynamic crystallization. Our synthesis successfully demonstrates that dynamic crystallization can be an alternative when the selectivity is not controlled by either kinetic or thermodynamic approaches in solution.

Original language	English
Journal	Journal of the American Chemical Society
DOIs	https://doi.org/10.1021/jacs.4c02338
Publication status	Accepted/In press - 2024

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.4c02338

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title = "Total Synthesis of Keramaphidin B and Ingenamine by Base-Catalyzed Diels-Alder Reaction Using Dynamic Regioselective Crystallization",

abstract = "The control of the selectivity is a central issue in the total synthesis of complex natural products. In this paper, we report the total synthesis of (±)-keramaphidin B and (±)-ingenamine. The key reaction is a DMAP-catalyzed Diels-Alder reaction in which the regioselectivity is completely controlled by dynamic crystallization. Our synthesis successfully demonstrates that dynamic crystallization can be an alternative when the selectivity is not controlled by either kinetic or thermodynamic approaches in solution.",

author = "Yuki Kurihara and Minori Yagi and Takashi Noguchi and Haruka Yasufuku and Ayane Okita and Sho Yoshimura and Takeshi Oishi and Noritaka Chida and Toshitaka Okamura and Takaaki Sato",

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journal = "Journal of the American Chemical Society",

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T1 - Total Synthesis of Keramaphidin B and Ingenamine by Base-Catalyzed Diels-Alder Reaction Using Dynamic Regioselective Crystallization

AU - Kurihara, Yuki

AU - Yagi, Minori

AU - Noguchi, Takashi

AU - Yasufuku, Haruka

AU - Okita, Ayane

AU - Yoshimura, Sho

AU - Oishi, Takeshi

AU - Chida, Noritaka

AU - Okamura, Toshitaka

AU - Sato, Takaaki

PY - 2024

Y1 - 2024

N2 - The control of the selectivity is a central issue in the total synthesis of complex natural products. In this paper, we report the total synthesis of (±)-keramaphidin B and (±)-ingenamine. The key reaction is a DMAP-catalyzed Diels-Alder reaction in which the regioselectivity is completely controlled by dynamic crystallization. Our synthesis successfully demonstrates that dynamic crystallization can be an alternative when the selectivity is not controlled by either kinetic or thermodynamic approaches in solution.

AB - The control of the selectivity is a central issue in the total synthesis of complex natural products. In this paper, we report the total synthesis of (±)-keramaphidin B and (±)-ingenamine. The key reaction is a DMAP-catalyzed Diels-Alder reaction in which the regioselectivity is completely controlled by dynamic crystallization. Our synthesis successfully demonstrates that dynamic crystallization can be an alternative when the selectivity is not controlled by either kinetic or thermodynamic approaches in solution.

UR - https://www.scopus.com/pages/publications/85190162233

UR - https://www.scopus.com/pages/publications/85190162233#tab=citedBy

U2 - 10.1021/jacs.4c02338

DO - 10.1021/jacs.4c02338

M3 - Article

AN - SCOPUS:85190162233

SN - 0002-7863

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

Total Synthesis of Keramaphidin B and Ingenamine by Base-Catalyzed Diels-Alder Reaction Using Dynamic Regioselective Crystallization

Abstract

ASJC Scopus subject areas

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