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Paper | Special issue | Vol 74, No. 1, 2007, pp.803-817
Published online, 9th November, 2007
DOI: 10.3987/COM-07-S(W)69
Synthesis of cis-Fused Pyranopyran and Pyranopyridine Templates by Ring Rearrangement Metathesis

Alexander Niethe and Siegfried Blechert*

*Institute of Chemistry, Technical University of Berlin, Strasse des 17. Juni 135, D-10623 Berlin, Germany

Abstract

A short, racemic and multigram scale synthesis of two novel templates is described. The key steps of the synthesis are ring rearrangement metathesis of strained tropane-derivatives into cis-fused pyranopyrans and pyranopyridines and subsequent functionalisation via cross metathesis and stereoselective dihydroxylation.