| Enantiomerically pure trans-beta-lactams from alpha-amino acids via compact fluorescent light (CFL) continuous-flow photolysis. | |
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MedLine Citation:
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PMID: 20698705 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Photolysis of alpha-diazo-N-methoxy-N-methyl (Weinreb) beta-ketoamides derived from enantiomerically pure (EP) alpha-amino acids affords the corresponding EP beta-lactams via an intramolecular Wolff rearrangement. The photochemistry is promoted with either standard UV irradiation or through the use of a 100 W compact fluorescent light; the latter affords a safe and environmentally friendly alternative to standard photolysis conditions. A continuous-flow photochemical reactor made from inexpensive laboratory equipment reduced reaction times and was amenable to scale-up. The diastereoselectivity (cis or trans) of the product beta-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, which is generally highly crystalline, has been developed. Evidence for C3 epimerization of Weinreb amide structures via a nonbasic, purely thermal route is presented. Subsequent transformations of both the Weinreb amide at C3 (beta-lactam numbering) and the amino acid side chain at C4 are well-tolerated, allowing for a versatile approach to diverse beta-lactam structures. The technology is showcased in the synthesis of a common intermediate used toward several carbapenem-derived structures starting from unfunctionalized aspartic acid. |
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Authors:
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Yvette S Mimieux Vaske; Maximillian E Mahoney; Joseph P Konopelski; David L Rogow; William J McDonald |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 132 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-08-11 Completed Date: 2010-11-30 Revised Date: 2013-04-12 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 11379-85 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry* Lactams / chemistry* Lighting / methods* Photolysis* Stereoisomerism Substrate Specificity |
| Grant Support | |
ID/Acronym/Agency:
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R25 GM058903-12/GM/NIGMS NIH HHS; R25GM58903/GM/NIGMS NIH HHS; S10RR019918/RR/NCRR NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Lactams |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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