Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 17, Pages 9023-9029Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01467
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- NIGMS NIH HHS [U54 GM104942] Funding Source: Medline
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A highly efficient asymmetric synthesis of the key tetrahydropyranol intermediate of DPP-4 inhibitor omarigliptin (1) is described. The successful development of a protecting-group- and precious-metal-free synthesis was achieved via the discovery of a practical asymmetric Henry reaction and the application of a one-pot nitro-Michael lactolization dehydration through-process. Other features of the synthesis include a highly efficient MsCI-mediated dehydration and a crystallization-induced dynamic resolution for exceptional ee and dr upgrade. The synthesis of this complex intermediate utilizes simple starting materials and proceeds in four linear steps.
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