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Total Synthesis of Orbiculamide A

Kayla C Newell¹, Cassandra M Sgarbi¹, Brian O Patrick¹

¹Chemistry Department, University of British Columbia, 2036 Main Mall, V6T 1Z1 Vancouver, BC, Canada.

Organic Letters

|April 9, 2026

Abstract:

Orbiculamide A, a macrocyclic peptide with antimitotic and antileukemic properties, contains several synthetically challenging structural motifs, including a 2-bromo-5-hydroxytryptophan residue, that presents a widely recognized synthetic challenge. Here, we report the first total synthesis of orbiculamide A, where central to our approach is a chemoselective, late-stage bromodesilylation strategy. This work provides a foundation for the synthesis of related natural products and scaffold diversification of medicinal peptides.

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