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 Citations (Scopus)

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
StatePublished - Nov 1 2013

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phloroglucinol
Phloroglucinol
nonanes
octanes
activity (biology)
cultured cells
cascades
reactivity
Cells
Cell Line
octane
hyperforin
bicyclo(3.3.1)nonane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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

In: Organic Letters, Vol. 15, No. 21, 01.11.2013, p. 5404-5407.

Research output: Contribution to journalArticle

Vidali, Veroniki P. ; Mitsopoulou, Kornilia P. ; Dakanali, Marianna ; Demadis, Konstantinos D. ; Odysseos, Andreani D. ; Christou, Yiota A. ; Couladouros, Elias A. / 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. In: Organic Letters. 2013 ; Vol. 15, No. 21. pp. 5404-5407.
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