Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application to Synthesize the Proposed Structure of Spiropreussione A

Hirokazu Tsukamoto; Yumi Nomura; Koichi Fujiwara; Shogo Hanada; Takayuki Doi

doi:10.1021/acs.orglett.8b01259

Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application to Synthesize the Proposed Structure of Spiropreussione A

Hirokazu Tsukamoto, Yumi Nomura, Koichi Fujiwara, Shogo Hanada, Takayuki Doi

PHA - Molecular Pharmaceutical Science

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

5 Citations (Scopus)

Abstract

A conjugate addition of diverse nucleophiles to acylketene acetals derived from 1,8-dihydroxynaphthalene (DHN) is developed for the formation of its 3-oxoalkan-1-one acetals. The initial acylketene acetals are prepared via double oxa-Michael addition of DHN to 1-bromo-1-propyn-3-ones. Carbonucleophiles, including organocopper reagents and active methylene compounds, and heteroatom nucleophiles were introduced under basic conditions. This method is applied for synthesizing spiropreussione A; the proposed structure does not correspond to that of the authentic natural product.

Original language	English
Pages (from-to)	3140-3143
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.8b01259
Publication status	Published - 2018 May 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application to Synthesize the Proposed Structure of Spiropreussione A. / Tsukamoto, Hirokazu; Nomura, Yumi; Fujiwara, Koichi; Hanada, Shogo; Doi, Takayuki.

In: Organic letters, Vol. 20, No. 10, 18.05.2018, p. 3140-3143.

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

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abstract = "A conjugate addition of diverse nucleophiles to acylketene acetals derived from 1,8-dihydroxynaphthalene (DHN) is developed for the formation of its 3-oxoalkan-1-one acetals. The initial acylketene acetals are prepared via double oxa-Michael addition of DHN to 1-bromo-1-propyn-3-ones. Carbonucleophiles, including organocopper reagents and active methylene compounds, and heteroatom nucleophiles were introduced under basic conditions. This method is applied for synthesizing spiropreussione A; the proposed structure does not correspond to that of the authentic natural product.",

author = "Hirokazu Tsukamoto and Yumi Nomura and Koichi Fujiwara and Shogo Hanada and Takayuki Doi",

note = "Funding Information: This work was partly supported by the Suntry Foundation for Life Sciences, the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED (under Grant Nos. JP18am0101095 and JP18am0101100) and JSPS KAKENHI (Grant No. JP15H05837 in Middle Molecular Strategy). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Tsukamoto, Hirokazu

AU - Nomura, Yumi

AU - Fujiwara, Koichi

AU - Hanada, Shogo

AU - Doi, Takayuki

N1 - Funding Information: This work was partly supported by the Suntry Foundation for Life Sciences, the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED (under Grant Nos. JP18am0101095 and JP18am0101100) and JSPS KAKENHI (Grant No. JP15H05837 in Middle Molecular Strategy). Publisher Copyright: © 2018 American Chemical Society.

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AB - A conjugate addition of diverse nucleophiles to acylketene acetals derived from 1,8-dihydroxynaphthalene (DHN) is developed for the formation of its 3-oxoalkan-1-one acetals. The initial acylketene acetals are prepared via double oxa-Michael addition of DHN to 1-bromo-1-propyn-3-ones. Carbonucleophiles, including organocopper reagents and active methylene compounds, and heteroatom nucleophiles were introduced under basic conditions. This method is applied for synthesizing spiropreussione A; the proposed structure does not correspond to that of the authentic natural product.

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Conjugate Addition to Acylketene Acetals Derived from 1,8-Dihydroxynaphthalene and Its Application to Synthesize the Proposed Structure of Spiropreussione A

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