SYNTHESIS OF STREPTAZOLIN - USE OF THE AZA-FERRIER REACTION IN CONJUNCTION WITH THE INOC PROCESS TO DELIVER A UNIQUE BUT SENSITIVE NATURAL PRODUCT

The total synthesis of the unique alkaloid natural product streptazolin is described. The synthetic route makes use of the Ferrier-like reaction of a Δ12-piperidinol with allyltrimethylsilane in combination with the INOC reaction to create the ring skeleton of this product. The extension of the aza-Ferrier reaction to other nucleophiles is discussed. The transformation of isoxazolines with peracids to β-hydroxy ketones or diol monoacetates discovered during the course of these studies is also presented. © 1990, American Chemical Society. All rights reserved.