Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole

被引:19
作者
Gilchrist, TL
Lemos, A
Ottaway, CJ
机构
[1] Chemistry Department, University of Liverpool, Liverpool
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 20期
关键词
D O I
10.1039/a703170j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The azabicyclo[3.2.0]heptan-7-ones 4, 10, 16 and 24 have been prepared from pyrrole. The same general approach has been used for all these derivatives; namely, substitution of pyrrole at the 2- and 5-carbon atoms, catalytic hydrogenation to produce pyrrolidine-2-acetic acid derivatives, and cyclisation using tris(1,3-dihydro-2-oxobenzoxazol-3-yl)phosphine oxide 6. The catalytic hydrogenation of 2,5-disubstituted pyrroles gives only the corresponding cis-2,5-disubstituted pyrrolidines. The hydrogenation proceeds more easily when the nitrogen atom bears a tert-butoxycarbonyl substituent. The N-tert-butoxycarbonylpyrroles 8 and 21 bearing an a-substituent in the acetate side chain were hydrogenated with a high degree of facial stereoselectivity. This allowed the 6-phthalimidoazabicyclo-[3.2.0]heptan-7-one 24 to be isolated as a single diastereoisomer. The X-ray crystal structure of a precursor, the triester, 22a, has been obtained.
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页码:3005 / 3012
页数:8
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