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Chiral synthesis of statine
Authors:Peter W.K. Woo
Affiliation:Warner-Lambert/Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan 48105 U.S.A.
Abstract:Statine (8a) has been obtained in high enantiomeric purity as its N-Boc-ethyl ester (8b) in a chiral synthesis. The sequence involves the enantio- and erythro-selective aldol condensation of N-Boc-L-leucinal (5) with (S)-4-(1-methylethyl)-3-[(methylthio)acetyl]-2-oxazolidinone (1) via the boron enolate, followed by desulfurization and saponification in ethanol, according to the methodology of Evans.
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