Divergent Syntheses of Pumiliotoxin‐Type Poison‐Frog Alkaloids

ChemistrySelect
2021.0

Abstract

Over 800 lipophilic alkaloids have been detected from the skin extracts of poison frogs. Pumiliotoxins (PTXs) are a large class of poison-frog alkaloids, and various congeners of PTXs have been detected to date. However, no exhaustive and effective syntheses of PTXs and their congeners have been reported. Herein, we describe the divergent syntheses of PTX 209F, hPTX 223G, 8-deoxy-PTX 193H, 9-deoxy-hPTX 207O, 8-desmethyl-PTX 195, and 9-desmethyl-hPTX 209H from the common chiral building block (2R,3S)-ethyl 1-allyl-3-hydroxy-6-oxopiperidine-2-carboxylate (−)-1. © 2021 Wiley-VCH GmbH

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