A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A

Stephan Knüppel, Victor O. Rogachev, Peter Metz

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Using a combined organocatalytic/metal-catalyzed strategy, the enantiopure title hydroazulenes were prepared in only four steps from (S)- and (R)-citronellal, respectively. A catalyst-controlled diastereoselective Michael addition of these aldehydes to methyl vinyl ketone followed by chemoselective dibromoolefination and one-pot Wittig olefination/alkyne formation afforded the key dienynes that underwent regioselective domino metathesis to yield the target natural products. A combination of an organocatalytic Michael addition and a ruthenium-catalyzed dienyne metathesis allowed efficient access to the enantiopure title hydroazulenes from (S)- and (R)-citronellal, respectively, in only four steps.

Original languageEnglish
Pages (from-to)6145-6148
Number of pages4
JournalEuropean Journal of Organic Chemistry
Issue number32
DOIs
Publication statusPublished - 1 Nov 2010
Externally publishedYes

Keywords

  • Domino reactions
  • Metathesis
  • Michael addition
  • Organocatalysis
  • Ruthenium
  • Terpenoids

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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