Synthesis of bicyclic carbamates as precursors of Sedum alkaloid derivatives

Z. Szakonyi, Matthias D'Hooghe, Iván Kanizsai, F. Fülöp, Norbert De Kimpe

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Synthesis of a N-Boc-protected piperidin-2-yl phosphine oxide starting from piperidine in three steps, followed by olefination using a variety of α,β-unsaturated aldehydes resulted in tert-butyl 2-(2′- alkenylidene)piperidine-1-carboxylates in high yields. A novel type of intramolecular cyclization of these enamides furnished a new family of 3-alkyl-4,6,7,8-tetrahydro-3H-pyrido[1,2-c][1,3]oxazin-1-ones as useful substrates for further elaboration. Subsequent reduction of these unsaturated bicyclic carbamates using NaCNBH3 or NaBH4 afforded the corresponding 3-alkylhexahydropyrido[1,2-c][1,3]oxazin-1-ones in a highly stereoselective way. Reductive ring opening of two representatives furnished the corresponding Sedum alkaloid derivatives in good yields.

Original languageEnglish
Pages (from-to)1595-1602
Number of pages8
JournalTetrahedron
Volume61
Issue number6
DOIs
Publication statusPublished - Feb 7 2005

Fingerprint

Sedum
phosphine
Carbamates
Alkaloids
Derivatives
Cyclization
Aldehydes
Oxides
Substrates
piperidine

Keywords

  • Bicyclic carbamate
  • Enamide
  • Sedum alkaloid
  • Stereoselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of bicyclic carbamates as precursors of Sedum alkaloid derivatives. / Szakonyi, Z.; D'Hooghe, Matthias; Kanizsai, Iván; Fülöp, F.; De Kimpe, Norbert.

In: Tetrahedron, Vol. 61, No. 6, 07.02.2005, p. 1595-1602.

Research output: Contribution to journalArticle

Szakonyi, Z. ; D'Hooghe, Matthias ; Kanizsai, Iván ; Fülöp, F. ; De Kimpe, Norbert. / Synthesis of bicyclic carbamates as precursors of Sedum alkaloid derivatives. In: Tetrahedron. 2005 ; Vol. 61, No. 6. pp. 1595-1602.
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