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Updated: Jun 11, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Ring Expansion via One-Pot Conversion of Lactone Acetals to Cyclic Enones. Synthesis of (±)-1-epi-Xerantholide
Jose Salvatierra1, Natalie A Silberberg1, Thomas G Minehan1
1Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, California 91330-8262, United States.
Abstract:
Baeyer-Villiger oxidation of α-alkoxy ketones 1 provides lactone acetals 2, which react with the lithium salts of dimethyl(alkyl) phosphonates in the presence of LaCl3·2LiCl to provide cyclic enones 3 in good to excellent yields after treatment with dilute aqueous potassium carbonate. Thus, five-, six-, and seven-membered lactones are converted to five-, six-, and seven-membered cyclic enones. The utility of this two-step ring expansion method is demonstrated in the synthesis of (±)-1-epi-xerantholide from 5-methyl-2-cyclohexen-1-one.
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