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Divergent Syntheses of Pumiliotoxin‐Type Poison‐Frog Alkaloids
Author(s) -
Okada Takuya,
Ozaki Takanori,
Yamamoto Taiga,
Kasahara Hirofumi,
Kawasaki Masashi,
Toyooka Naoki
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004825
Subject(s) - desmethyl , stereochemistry , chemistry , biochemistry , metabolite
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 (2 R ,3 S )‐ethyl 1‐allyl‐3‐hydroxy‐6‐oxopiperidine‐2‐carboxylate (−)‐ 1 .