Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Shuichi Hagihara; Kengo Hanaya; Takeshi Sugai; Mitsuru Shoji

doi:10.1038/ja.2017.91

Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Shuichi Hagihara, Kengo Hanaya, Takeshi Sugai, Mitsuru Shoji

School of Pharmaceutical Sciences

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

7 Citations (Scopus)

Abstract

Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

Original language	English
Pages (from-to)	257-262
Number of pages	6
Journal	Journal of Antibiotics
Volume	71
Issue number	2
DOIs	https://doi.org/10.1038/ja.2017.91
Publication status	Published - 2018 Feb 1

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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

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10.1038/ja.2017.91

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abstract = "Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.",

author = "Shuichi Hagihara and Kengo Hanaya and Takeshi Sugai and Mitsuru Shoji",

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AU - Sugai, Takeshi

AU - Shoji, Mitsuru

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AB - Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

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Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

Abstract

ASJC Scopus subject areas

UN SDGs

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