Studies toward Pestalachloride B: Synthesis of the 6/7/6 Tricyclic Scaffold
Year: 2026
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Antibiotic therapy is a critical part of modern healthcare, and the discovery of antibiotics with novel mechanisms of action is needed to combat the rise of antimicrobial resistance. Pestalachloride B, isolated from Pestalotiopsis adusta, is a compound belonging to the pestalone family of natural products which demonstrates potent and selective antimicrobial activity against clinically relevant, antimicrobial-resistant Gram-positive bacteria. Here, we report the first synthetic studies focused specifically on pestalachloride B. Two key disconnections were evaluated for the construction of the rare 6/7/6 tricyclic scaffold, and a key intramolecular Parham-type cyclization was found to afford the desired scaffold in 74% yield, enabling us to obtain a late-stage intermediate bearing the complete pestalachloride B framework in 8% overall yield over 11 steps.
Source: Organic Letters
Authors: Benjamin E. Deprez, Andrew R. LeBlanc, Qimin Winnie Yang, Alexander P. Smith, William M. Wuest
Institution: Emory University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Funders: Medicinal Chemistry Division, American Chemical Society, National Science Foundation, Emory University, National Institutes of Health, National Institute of General Medical Sciences, National Institute of Allergy and Infectious Diseases, National Institute of Diabetes and Digestive and Kidney Diseases, Division of Chemistry
OpenAlex ID: W7130509390