Synthesis of a 1-oxacephem structurally related to clavulanic acid from D-glucuronolactone.

被引：17

作者：

Furman, B

Molotov, S

Thurmer, R

Kaluza, Z

Voelter, W

Chmielewski, M

机构：

[1] POLISH ACAD SCI,INST ORGAN CHEM,PL-01224 WARSAW,POLAND

[2] RUSSIAN ACAD SCI,ZIELINSKY INST ORGAN CHEM,HIGHER CHEM COLL,MOSCOW,RUSSIA

[3] UNIV TUBINGEN,INST PHYS CHEM,D-72076 TUBINGEN,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 16期

关键词：

D O I：

10.1016/S0040-4020(97)00248-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[2+2]Cycloaddition of chlorosulfonyl isocyanate to 3-O-vinyl ethers derived from D-glucose and D-glucuronolactone proceeded with an excellent stereoselectivity to provide azetidin-2-ones with (R) configuration at C-4'. Intramolecular N-alkylation afforded 1-oxabicyclic-beta-lactams having six- or seven-membered ring fused to the four-membered one. (C) 1997 Elsevier Science Ltd.

引用

页码：5883 / 5890

页数：8

共 20 条

[1] Preparations of two pivotal intermediates for the synthesis of 1-beta-methyl carbapenem antibiotics [J].