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Enantioselective synthesis of isotopically labeled homocitric acid lactone.

ABSTRACT: A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically (13)C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.

SUBMITTER: Moore JT 

PROVIDER: S-EPMC3932135 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of isotopically labeled homocitric acid lactone.

Moore Jared T JT   Hanhan Nadine V NV   Mahoney Maximillian E ME   Cramer Stephen P SP   Shaw Jared T JT  

Organic letters 20131101 22

A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically (13)C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement. ...[more]

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