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

研究成果: Article査読

4 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3140-3143
ページ数4
ジャーナルOrganic letters
20
10
DOI
出版ステータスPublished - 2018 5 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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