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

研究成果: Article › 査読

26 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	1059-1062
ページ数	4
ジャーナル	Tetrahedron Letters
巻	35
号	7
DOI	https://doi.org/10.1016/S0040-4039(00)79965-5
出版ステータス	Published - 1994 2月 14
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4039(00)79965-5

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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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AU - Taguchi, Takeo

PY - 1994/2/14

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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

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