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Updated: May 24, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Total Synthesis and Stereochemical Proposal of the Hexaene Framework of Bacillaene
Maximilian Guhlke1, Johannes Herbst1, Tra Giang Nguyen1
1Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, D-53121 Bonn, Germany.
Abstract:
The central hexaene core of the labile polyene antibiotic bacillaene bearing three Z-configured olefins was prepared with excellent geometrical purity by an iterative cross-coupling strategy, involving improved syntheses of bimetallic reagents and efficient protocols for stereoselective polyene generation, revealing insights into the origin of bacillaene's instability. Furthermore, a useful method for monitoring polyene iteration by UV-vis shift analyses and the absolute stereochemistry of this core by biosynthetic gene cluster analysis are reported.
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