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

Osamu Kitagawa; Tadashi Inoue; Takeo Taguchi

doi:10.1016/S0040-4039(00)79965-5

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

Osamu Kitagawa, Tadashi Inoue, Takeo Taguchi

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1059-1062
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4039(00)79965-5
Publication status	Published - 1994 Feb 14
Externally published	Yes

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Kitagawa, O., Inoue, T., & Taguchi, T. (1994). Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives: Application to cyclosarkomycin synthesis. Tetrahedron Letters, 35(7), 1059-1062. https://doi.org/10.1016/S0040-4039(00)79965-5

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10.1016/S0040-4039(00)79965-5