Total Synthesis of Spiromamakone A and Structure Revision of Spiropreussione A

Hirokazu Tsukamoto, Shogo Hanada, Yumi Nomura, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Spiromamakone A is a racemic natural product having a naphthyl acetal group on a spiro[4,4]nonadiene skeleton. Its total synthesis was achieved by double oxa-Michael addition of 1,8-dihydroxynaphthalene to 2-(1-bromoalkylidene)-4-isopropoxy-4-cyclopentene-1,3-dione, which was prepared by palladium(II)-catalyzed ring expansion of 4-(1-alkynyl)-4-hydroxy-3-isopropoxy-2-cyclobuten-1-one, and a subsequent intramolecular aldol reaction. The synthesis using optically active intermediates enabled identification of the racemization step of spiromamakone A and revealed that spiromamakone A and spiropreussione A are identical; the latter had been reported as a constitutional isomer of the other.

Original languageEnglish
Pages (from-to)9430-9441
Number of pages12
JournalJournal of Organic Chemistry
Volume83
Issue number16
DOIs
Publication statusPublished - 2018 Aug 17

ASJC Scopus subject areas

  • Organic Chemistry

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