An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Tadashi Hanaya; Chika Itoh

doi:10.3987/COM-10-S(E)80

An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Tadashi Hanaya, Chika Itoh

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

Original language	English
Pages (from-to)	1675-1683
Number of pages	9
Journal	Heterocycles
Volume	82
Issue number	2
DOIs	https://doi.org/10.3987/COM-10-S(E)80
Publication status	Published - Feb 28 2010

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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AU - Hanaya, Tadashi

AU - Itoh, Chika

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Y1 - 2010/2/28

N2 - N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

AB - N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

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An efficient synthesis of antibiotic SF-2312 (3-dihydroxyphosphoryl-1,5- dihydroxy-2-pyrrolidone)

Abstract

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