An unusual michael-induced skeletal rearrangement of a bicyclo[3.3.1]nonane framework of phloroglucinols to a novel bioactive bicyclo[3.3.0]octane

Veroniki P. Vidali, Kornilia P. Mitsopoulou, Marianna Dakanali, Konstantinos D. Demadis, Andreani D. Odysseos, Yiota A. Christou, Elias A. Couladouros

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

A novel skeletal rearrangement of bicyclo[3.3.1]nonane-2,4,9-trione (16) to an unprecedented highly functionalized bicyclo[3.3.0]octane system (17), induced by an intramolecular Michael addition, is presented. This novel framework was found to be similarly active to hyperforin (1), against PC-3 cell lines. A mechanistic study was examined in detail, proposing a number of cascade transformations. Also, reactivity of the Δ7,10-double bond was examined under several conditions to explain the above results.

Original languageEnglish (US)
Pages (from-to)5404-5407
Number of pages4
JournalOrganic Letters
Volume15
Issue number21
DOIs
Publication statusPublished - Nov 1 2013

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this