Synthesis of the Aromatic and Monosaccharide Moieties of Staurosporine

Richard P. Joyce, James A. Gainor, Steven M. Weinreb

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98 Scopus citations

Abstract

Efficient synthetic routes have been developed for the heteroaromatic unit 4 and some aminohexoses similar to 5, which are structural fragments of staurosporine (1). Aromatic lactone 4 has been prepared in four steps from 3,4-dibromomaleimide in good overall yield. A strategy utilizing Diels-Alder [4 + 2] cycloadditions of benzyl sulfinylcarbamate was used to synthesize staurosporine amino sugars in both the pyranose form 37 and in acyclic versions 38, 41, and 42. A novel feature of the work involved stereospecific syn epoxidations of the 3,6-di-hydrothiazine oxide adducts 15 and 16 directed by the sulfinyl oxygen.

Original languageEnglish (US)
Pages (from-to)1177-1185
Number of pages9
JournalJournal of Organic Chemistry
Volume52
Issue number7
DOIs
StatePublished - Apr 1 1987

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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