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

20 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

Fingerprint

metathesis
routes
Alkynes
Ruthenium
alkynes
Biological Products
aldehydes
Aldehydes
ketones
ruthenium
Metals
catalysts
Catalysts
products
metals
citronellal
clavukerin A
isoclavukerin
3-buten-2-one

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A. / Knüppel, Stephan; Rogachev, Victor O.; Metz, Peter.

In: European Journal of Organic Chemistry, No. 32, 01.11.2010, p. 6145-6148.

Research output: Contribution to journalArticle

Knüppel, Stephan ; Rogachev, Victor O. ; Metz, Peter. / A concise catalytic route to the marine sesquiterpenoids (-)-clavukerin A and (-)-isoclavukerin A. In: European Journal of Organic Chemistry. 2010 ; No. 32. pp. 6145-6148.
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