A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R

Felix W.W. Hartrampf, Takayuki Furukawa, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramine R is presented. It relies on a base-mediated cyclization that resembles the Conia-ene reaction of ynones and gold-catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.

Original languageEnglish (US)
Pages (from-to)893-896
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number3
DOIs
StatePublished - 2017

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Bearings (structural)
Alkaloids
Cyclization
Alkenes
Precious metals
Gold
Catalysis
Olefins
Substrates
Temperature
lycoposerramine R

Keywords

  • alkynes
  • Conia-ene reaction
  • hydrindanes
  • lycopodium alkaloids
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R. / Hartrampf, Felix W.W.; Furukawa, Takayuki; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 56, No. 3, 2017, p. 893-896.

Research output: Contribution to journalArticle

Hartrampf, Felix W.W. ; Furukawa, Takayuki ; Trauner, Dirk. / A Conia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (−)-Lycoposerramine R. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 3. pp. 893-896.
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