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Asymmetric Synthesis of Homocitric Acid Lactone.

ABSTRACT: 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.

SUBMITTER: Nickerson LA

PROVIDER: S-EPMC7190193 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of Homocitric Acid Lactone.

Nickerson Leslie A LA Huynh Valerie V Balmond Edward I EI Cramer Stephen P SP Shaw Jared T JT

The Journal of organic chemistry 20161021 22

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. ...[more]

PMID: 27685496

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