New routes to clavine-type ergot alkaloids. Part 2: Synthesis of the last, so far not yet synthesized member of the clavine alkaloid family, (±)-cycloclavine

Mária Incze, Gábor Dörnyei, István Moldvai, Eszter Temesvári-Major, Orsolya Egyed, Csaba Szántay

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Starting from 4-bromo-Uhle's ketone (2), an alkylation step using ethyl 3-methylamino-propionate followed by intramolecular aldol condensation in two steps, transformation of the ester group into a methyl group, and finally cyclopropanation of the 8,9 double bond, resulted in a six-step total synthesis of (±)-cycloclavine (1).

Original languageEnglish
Pages (from-to)2924-2929
Number of pages6
JournalTetrahedron
Volume64
Issue number13
DOIs
Publication statusPublished - Mar 24 2008

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Keywords

  • (±)-Cycloclavine
  • Clavine alkaloids
  • Cyclopropanation with diazomethane
  • Modified intramolecular Reformatsky-type cyclization
  • Total synthesis from 4-bromo-Uhle's ketone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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