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
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
收藏
页码:7385 / 7392
页数:8
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