Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization

Kentaro Yaji, Mitsuru Shindo

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A synthetic study of the Stemona alkaloid stemonamide is described. The FeCl3-promoted fast Nazarov reaction of β-alkoxy divinyl ketones in the presence of t-BuOH afforded an α-methylene cyclopentenone, which was subsequently subjected to the Rh-catalyzed C-H amination to provide a fully appropriately substituted α-methylene cyclopentenone as the core skeleton of stemonamide.

Original languageEnglish
Pages (from-to)5469-5472
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number41
DOIs
Publication statusPublished - Oct 13 2010

Fingerprint

Cyclization
Skeleton
Stemonaceae
Amination
Ketones
Alkaloids
stemonamide
cyclopentenone
alkoxyl radical
1,3-butadiene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization. / Yaji, Kentaro; Shindo, Mitsuru.

In: Tetrahedron Letters, Vol. 51, No. 41, 13.10.2010, p. 5469-5472.

Research output: Contribution to journalArticle

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