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, O. Egyed, Csaba Szántay

Research output: Contribution to journalArticle

25 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

Fingerprint

Ergot Alkaloids
Propionates
Alkylation
Ketones
Condensation
Esters
cycloclavine
3-hydroxybutanal

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
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Incze, Mária; Dörnyei, Gábor; Moldvai, István; Temesvári-Major, Eszter; Egyed, O.; Szántay, Csaba.

In: Tetrahedron, Vol. 64, No. 13, 24.03.2008, p. 2924-2929.

Research output: Contribution to journalArticle

Incze, Mária ; Dörnyei, Gábor ; Moldvai, István ; Temesvári-Major, Eszter ; Egyed, O. ; Szántay, Csaba. / 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. In: Tetrahedron. 2008 ; Vol. 64, No. 13. pp. 2924-2929.
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