The Nicholas approach to natural product hybrids

Elsa Álvaro, María C. De La Torre*, Miguel A. Sierra

*Corresponding author for this work

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

The intermolecular Nicholas reaction of terpene-based scaffolds is an excellent access to natural product hybrid compounds. These intermolecular reactions have a low selectivity and are scarcely efficient for non-conjugated cations, but they are highly efficient to produce new terpene structures through an intramolecular reaction pathway. The use of cations derived from natural product derived [Co2(CO)6]-enyne complexes is, in contrast, a highly efficient regio- and stereoselective procedure to prepare very complex structures, incorporating diverse densely functionalized or labile moieties. Thus, β-pinene-diterpene-alkaloid or homohybrids can be accessed in totally stereo-, regio- and siteselective fashion. This approach efficiently discriminates between different propargylic positions by selecting the nature of the alcohol, being the enyne-derived cations the most reactive. The chimera 38 with a steroid-terpene-indole skeleton was prepared in this way.

Original languageEnglish (US)
Pages (from-to)6403-6411
Number of pages9
JournalChemistry - A European Journal
Volume12
Issue number24
DOIs
StatePublished - Aug 16 2006

Keywords

  • Cobalt
  • Hybrids
  • Natural products
  • Nicholas reaction
  • Synthesis

ASJC Scopus subject areas

  • Chemistry(all)

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