The formylacetate synthon. Studies related to the synthesis of the penam and oxapenam ring systems
作者:
Saul Wolfe,
Roman Z. Sterzycki,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1987)
卷期:
Volume 65,
issue 1
页码: 26-30
ISSN:0008-4042
年代: 1987
DOI:10.1139/v87-006
出版商: NRC Research Press
数据来源: NRC
摘要:
Methyl penicillanate has been synthesized by condensation ofD-penicillamine with three different variations of the synthon RO2CCH2CHO, followed by esterification of the resulting 4-carboxythiazolidine-2-acetic acid ester, removal of R, and Mukaiyama ring closure. The conditions for the synthesis of an analogous 4-carboxyoxazolidine-2-acetic acid ester, containing anN-benzoyl protecting group, have been worked out. The condensation of threonine with diethinylketone does not lead directly to a vinylogous oxapenam.
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