Asymmetric Synthesis of Homocitric Acid Lactone.
A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
Leslie A
LA
Nickerson
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
Valerie
V
Huynh
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
Edward I
EI
Balmond
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
Stephen P
SP
Cramer
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
Jared T
JT
Shaw
D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism
D007783:Lactones; C070684:homocitrate lactone
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