Diastereoselective Total Synthesis of Sibirine via Functionalized Imine Precursors

M. Keppens; N. De Kimpe

doi:10.1055/s-1994-22830

Synlett 1994; 1994(4): 285-286
DOI: 10.1055/s-1994-22830

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Diastereoselective Total Synthesis of Sibirine via Functionalized Imine Precursors

M. Keppens^* , N. De Kimpe

^*Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, B-9000 Gent, Belgium

Abstract

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The spirocyclic alkaloid (±)-sibirine was prepared in a straightforward way from an easily accessible imine precursor. A stabase-mediated alkylation and cyclization process provided an azaspirocyclic intermediate, which was converted stereoselectively to (±)-sibirine via a convenient four step sequence including a stereoselective cerium-catalyzed reduction. The first two steps of this sequence also constitute a formal synthesis of (±)-nitramine.

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