Concise total syntheses of phelligridins A, C, and D

Takayuki Ohyoshi; Keisuke Mitsugi; Tatsuya Higuma; Fumitaka Ichimura; Masahito Yoshida; Hideo Kigoshi

doi:10.1039/C8RA10346A

Concise total syntheses of phelligridins A, C, and D†

Takayuki Ohyoshi,

*^a Keisuke Mitsugi,^a Tatsuya Higuma,^a Fumitaka Ichimura,^a Masahito Yoshida

^a and Hideo Kigoshi

*^a

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* Corresponding authors

^a Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571, Japan
E-mail: kigoshi@chem.tsukuba.ac.jp, ohyoshi@chem.tsukuba.ac.jp

Abstract

We have established a concise and scalable synthetic pathway for phelligridins A (1), C (2) and D (3). The synthetic highlights were Suzuki–Miyaura coupling and aldol-type condensation of α-pyrone. Phelligridin A was synthesized in four steps, while phelligridins C and D were each synthesized in six steps. Furthermore, we have revealed that the whole structure is essential for the cytotoxicity of phelligridins.

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https://doi.org/10.1039/C8RA10346A

Submitted

17 Dec 2018

Accepted

19 Feb 2019

First published

05 Mar 2019

This article is Open Access

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RSC Adv., 2019,9, 7321-7323

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Concise total syntheses of phelligridins A, C, and D

T. Ohyoshi, K. Mitsugi, T. Higuma, F. Ichimura, M. Yoshida and H. Kigoshi, RSC Adv., 2019, 9, 7321

DOI: 10.1039/C8RA10346A

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Concise total syntheses of phelligridins A, C, and D†

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Concise total syntheses of phelligridins A, C, and D

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