Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene

Hirokazu Tsukamoto, Shogo Hanada, Koichi Kumasaka, Noritaka Kagaya, Miho Izumikawa, Kazuo Shin-Ya, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Two benzo analogues of cytotoxic spiromamakone A, comprising carbon atoms with the same oxidation state and unsaturation degree as those of the natural products, are synthesized and biologically evaluated. Substitution of α,α′-dioxoketene dithioacetals, derived from 1,3-cyclopentanediones with protected (2-formylphenyl)magnesium bromide and 1,8-dihydroxynaphthalene, followed by deprotection, generated these analogues via an intramolecular aldol reaction. The cytotoxicity of benzo analogues and synthetic intermediates against cervical carcinoma HeLa cells shows the necessity of the 4-cyclopentene-1,3-dione moiety for biological activity.

Original languageEnglish
Pages (from-to)4848-4851
Number of pages4
JournalOrganic letters
Volume18
Issue number19
DOIs
Publication statusPublished - 2016 Oct 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene'. Together they form a unique fingerprint.

Cite this