title: A Single-Flask Synthesis of Morita-Baylis-Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E.
abstract: Sequential treatment of (ethoxyethynyl)lithium with aldehydes and/or ketones (2 and 4) and BF3·OEt2 gives rise to β-hydroxyenoates 5 in good to excellent overall yields. Similarly, the combination of 1 (M = Li) and dicarbonyl compounds 6 (X = O) or keto/aldehyde acetals (X = OMe) followed by the addition of a Lewis acid leads to five-, six-, and seven-membered hydroxycycloalkene carboxyates. The utility of this method is demonstrated in the synthesis of the α-alkylidene lactone natural products subamolide D and E.
authors.affiliation: Department of Chemistry and Biochemistry, California State University , Northridge 18111 Nordhoff Street, Northridge, California 91330-8262, United States.
authors.forename: Kevin
authors.initials: K
authors.lastname: Ng
authors.affiliation: Department of Chemistry and Biochemistry, California State University , Northridge 18111 Nordhoff Street, Northridge, California 91330-8262, United States.
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan