Robert M. Borzilleri

Synthesis of appropriately functionalized vancomycin CD and DE ring systems

Abstract Synthesis of appropriately and fully functionalized 16-membered CD and DE ring systems of vancomycin is detailed.

An unusually facile SnAr 14-membered biaryl ether macrocyclization reaction suitable for preparation of the cycloisodityrosine subunit of bouvardin, deoxybouvardin and related agents

Abstract A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed based on a key intramolecular SnAr biaryl ether ring closure.

Synthesis of (9S,12S)-cycloisodityrosine and its unnatural (9R,12S)-diastereomer

Abstract A synthesis of the (9 S ,12 S )-cycloisodityrosine derivatives and their unnatural (9 R ,12 S )-diastereomers are disclosed. The approach is based on an intramolecular aromatic nucleophilic substitution reaction for formation of the macrocyclic biaryl ether and includes the documentation of a remarkably facile base-catalyzed epimerization.