A new synthetic approach to dendrobatid alkaloids

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Abstract
A remarkably high regio- and stetreoselective approach for the syntheses of (+)-allopumiliotoxin alkaloids 267A and 339A based on intramolecular nickel(II)/chromium( 11)-mediated ring closure has been developed. South American poison-dart frogs of the family Dendrobatidae have been a rich source of various structurally unique alkaloids. Virtually all of these alkaloids possess high pharmacological activity on nerve and muscle. After the early discovery of four classes of dendrobatid alkaloids that are of the pumiliotoxin C class, the histrionicotoxins, gephyrotoxins, and batrachotoxins, new members of the pumiliotoxin A class and their allo series were isolated and structurally defined.* The latter subclass of alkaloids, the allopumiliotoxins, is a group of hydroxy congeners of the pumiliotoxin A class and they are the most complex members of the pumiliotoxin A alkaloid group.3 For several years, research efforts in our laboratory have been directed toward the development of chiral methods for the total syntheses of dendrobatid alkaloids.4 This article is concerned with the highly regio- and stereocontrolled approach to (+)-allopumiliotoxins 267A (1) and 339A (2).

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