Asymmetric Syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-Methano-2,6-diaminopimelic Acids. Studies Directed to the Design of Novel Substrate-based Inhibitors of L,L-Diaminopimelate Epimerase

The asymmetric syntheses ot (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal co...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 4; pp. 1149 - 1164
Main Authors Williams, Robert M., Fegley, Glenn J., Gallegos, Reneé, Schaefer, Felicity, Pruess, David L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2 FORMS
ENZYME 1-AMINOCYCLOPROPANE-1-CARBOXYLATE DEAMINASE
ESCHERICHIA-COLI
PROLINE RACEMASE
FRACTIONATION FACTORS
NUCLEOPHILIC ALKYLIDENE TRANSFER
ALPHA-AMINO-ACIDS
DIAMINOPIMELIC ACID
ANTI-TUMOR LACTONES
(DIALKYLAMINO)METHYLOXOSULFONIUM METHYLIDES
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Summary:The asymmetric syntheses ot (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal conditions. The asymmetric syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S -2,3-methano-2 6-diaminopimelic acids is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00976-0