Total Synthesis of (+)-laurencin: An Asymmetric Alkylation - Ring-closing Metathesis Approach to Medium Ring Ethers

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2029-2032

  Crimmins, Michael T ^a   Emmitte, Kyle A ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 BENZYL 3 BENZYLOXYACETYL 2 OXAZOLIDINONE; 4-BENZYL-3-BENZYLOXYACETYL-2-OXAZOLIDINONE; ALDEHYDE; ETHER DERIVATIVE; LAURENCIN; OXAZOLE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; OXOCIN DERIVATIVE;

ALKYLATION; ARTICLE; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKYLATION; ETHERS; ETHERS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; OXAZOLES; OXAZOLIDINONES; OXOCINS; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 0033576445     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991201e     Document Type: Article

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17. Compound 6 was prepared in one step from commercially available benzyloxyacetic acid and (S)-(+)-4-benzyl-2-oxazolidinone. See also: Evans, D. A.; Cage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961-1963.
18. 13C NMR, IR, and optical rotation. Yields are for isolated, chromatographically purified products.
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24. 27D = +70.2°). The low value of the specific rotation is presumably due to contamination of the sample with a minor amount of the cis enyne diastereomer of (+)-laurencin.