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

Research output: Contribution to journalArticlepeer-review

4 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 languageEnglish
Pages (from-to)3140-3143
Number of pages4
JournalOrganic letters
Volume20
Issue number10
DOIs
Publication statusPublished - 2018 May 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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