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Updated: Jun 4, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
11-Step enantioselective synthesis of (-)-lomaiviticin aglycon
Seth B Herzon1, Liang Lu, Christina M Woo
1Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA. seth.herzon@yale.edu
Abstract:
Lomaiviticins A and B are complex antitumor antibiotics that were isolated from a strain of Micromonospora. A confluence of several unusual structural features renders the lomaiviticins exceedingly challenging targets for chemical synthesis. We report an 11-step, enantioselective synthetic route to lomaiviticin aglycon. Our route proceeds by late-stage, stereoselective dimerization of two equivalent monomeric intermediates, a transformation that may share parallels with the natural products' biosyntheses. The route we describe is scalable and convergent, and it lays the foundation for determination of the mode of action of these natural products.
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