CHEMOENZYMATIC PREPARATION OF A KEY INTERMEDIATE FOR CARBAPENEM SYNTHESIS STARTING FROM ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-ASTERISK)

被引：18

作者：

BANFI, L ^{[1
]}

GUANTI, G ^{[1
]}

NARISANO, E ^{[1
]}

机构：

[1] CNR,CTR CHIM COMPOSTI CICLOALIFATICI & AROMAT,I-16132 GENOA,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(01)87214-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Unsubstituted 2-azetidinones 3a,b, which are useful intermediates for the synthesis of carbapenem antibiotics, have been enantiospecifically and diastereoselectively prepared starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) 4. a new chiral building block obtained through biological methods. The key steps are the highly diastereoselective addition of Me2CuLi to 4 (diast. ratio = 95 : 5), and the regioselective deblocking of tBuMe2Si ether in the presence of a (iPr)3Si ether, by using a novel methodology.

引用

页码：7385 / 7392

页数：8

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