α-Activated cross conjugated cycloalkenone systems in organic synthesis

Yen-Ku Wu, Tai Ei Ly, Kak Shan Shia*

*Corresponding author for this work

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Under catalysis with an appropriate Lewis acid, the intermolecular Diels-Alder cycloaddition and intramolecular polyene cyclization of the α-activated cross conjugated cycloalkenone systems, possessing particularly increased dienophilicity/electrophilicity in the cross conjugated double bond, proceeded constantly with a high degree of stereochemical control, leading to a variety of synthetically useful molecules, which may serve as advanced intermediates towards many structurally challenging natural products, especially cis-clerodane diterpenoids. Mechanistically, an additional conjugated double bond incorporated into the synthetically useful molecules, which may serve as advanced intermediates towards many structurally challenging natural products, especially cis-clerodane diterpenoids. Mechanistically, an additional conjugated double bond incorporated into the cycloalkenone core of the titled systems might contribute synergistically to the classical secondary orbital effects, thus significantly enhancing the endo-to-ketone addition. In addition, a tandem multiple-bond migration process, an enzymatic pathway prevalent in nature, was proposed to rationalize the formation of structurally unusual polyene-cyclization products occurring under standard chemical conditions.

Original languageEnglish
Pages (from-to)78-93
Number of pages16
JournalCurrent Organic Synthesis
Volume7
Issue number1
DOIs
StatePublished - 25 Jun 2010

Keywords

  • Cross conjugated
  • Cycloaddition
  • Diels-Alder reaction
  • Lewis acids
  • Polyene cyclization

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