Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives: Application to cyclosarkomycin synthesis

Osamu Kitagawa, Tadashi Inoue, Takeo Taguchi

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The iodocarbocyclization of 4-pentenylmalonate 1 having a substituent at the 2 or 3 position effectively proceeded by treating 1 with I2 and Ti(OtBu)4 in the presence of CuO. Stereoelectronic effect of the subtituent at allylic position on diastereoselectivity was notable. As an application of the present reaction, the efficient synthesis of cyclosarkomycin 7 was achieved.

Original languageEnglish
Pages (from-to)1059-1062
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number7
DOIs
Publication statusPublished - 1994 Feb 14
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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