AN EFFICIENT SYNTHESIS OF ANTIBIOTIC SF-2312 (3-DIHYDROXYPHOSPHORYL-1,5-DIHYDROXY-2-PYRROLIDONE)

被引：7

作者：

Hanaya, Tadashi ^{[1
]}

Itoh, Chika ^{[1
]}

机构：

[1] Okayama Univ, Dept Chem, Fac Sci, Okayama 7008530, Japan

来源：

HETEROCYCLES | 2011年 / 82卷 / 02期

关键词：

Phosphonic Acid; Hydroxamic Acid; Antibiotic; 2-Pyrrolidone; C-P Bond; PHOSPHONIC ACID ANTIBIOTICS; BIOLOGICAL EVALUATION; FOSMIDOMYCIN;

D O I：

10.3987/COM-10-S(E)80

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1675 / +

页数：10

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