Topological selectivity in the intramolecular [4+ 1] pyrroline annulation. Formal total stereospecific synthesis of (.+-.)-supinidine,(.+-.)-isoretronecanol, and (.+-.)- …

T Hudlicky, JO Frazier, G Seoane…

Index: Hudlicky,T.; Frazier,J.O.; Seoane,G. Journal of the American Chemical Society, 1986 ,  vol. 108, p. 3755            

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Citation Number: 91

Abstract

Abstract: The preparation and cycloadditions of azidodienes 13 and 14 are described in detail. The synthesis of pyrrolines 1 and 2 is reported, and the conditions are revealed to achieve maximum selectivity in their preparation. The topography of the ultimately prepared pyrrolines depends primarily on the substitution parameters of the starting dienes and on the conditions of rearrangement of their respective vinylaziridines 15 and 16. The former ...