Enantioselective synthesis of isotopically labeled homocitric acid lactone.
نویسندگان
چکیده
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.
منابع مشابه
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.
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عنوان ژورنال:
- Organic letters
دوره 15 22 شماره
صفحات -
تاریخ انتشار 2013