Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni

Takahisa Ogamino, Rika Obata, Hiroshi Tomoda, Shigeru Nishiyama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH 4] 2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.

Original languageEnglish
Pages (from-to)134-139
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume79
Issue number1
DOIs
Publication statusPublished - 2006

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Epoxy Compounds
Electrochemical oxidation
Phenol
Isomers
Oxygen
Derivatives
calafianin

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni. / Ogamino, Takahisa; Obata, Rika; Tomoda, Hiroshi; Nishiyama, Shigeru.

In: Bulletin of the Chemical Society of Japan, Vol. 79, No. 1, 2006, p. 134-139.

Research output: Contribution to journalArticle

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