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Synthetic studies directed toward the liposidomycins: Preparation and reactions of serine-derived epoxides

1995; Elsevier BV; Volume: 36; Issue: 37 Linguagem: Inglês

10.1016/00404-0399(50)1349-m

1873-3581

William Moore, Frederick A. Luzzio,

Synthetic Organic Chemistry Methods

The preparation of an oxiranyl serine derivative which will be incorporated into the diazepanone fragment of the liposidomycin B core subunit is described. Reactions of the epoxide with nitrogen nucleophiles afforded the 1,2-(O,N-protected)-4-N-functionalized-3-butanols in modest to good yields. A Mosher ester analysis of the alcohol resulting from azide promoted oxirane ring opening is also discussed.