Synthetic studies on (?)-lemonomycin: stereocontrolled construction of the 3,8-diazabicyclo[3.2.1] skeleton

Chemical Communications Pub Date: 2004-12-08 DOI: 10.1039/B415030A

Abstract

Stereoselective synthesis of the pentacyclic key intermediate 22 for (?)-lemonomycin (1) has been accomplished using the Ugi 4-CC reaction with our novel isocyanide 8, a cross-metathesis of 13 and allylsilane and a subsequent intramolecular Hosomi–Sakurai type reaction.

Graphical abstract: Synthetic studies on (?)-lemonomycin: stereocontrolled construction of the 3,8-diazabicyclo[3.2.1] skeleton
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