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 › peer-review

25 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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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T1 - Diastereoselective iodocarbocyclization of 4-pentenylmalonate derivatives

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AU - Kitagawa, Osamu

AU - Inoue, Tadashi

AU - Taguchi, Takeo

PY - 1994/2/14

Y1 - 1994/2/14

N2 - 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.

AB - 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.

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

Abstract

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