Tetrahedron

N-hydroxypyridine-2-thione carbamates. v. syntheses of alkaloid skeletons by aminium cation radical cyclizations

M Newcomb, DJ Marquardt, TM Deeb

Index: Newcomb, Martin; Marquardt, Donald J.; Deeb, Thomas M. Tetrahedron, 1990 , vol. 46, # 7 p. 2329 - 2344

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Citation Number: 75

Abstract

The title radical precursors (PTOC carbamates) were employed as sources of a variety of 5, 6-unsaturated aminium cation radicals. 5-Exo radical cyclization followed by trapping by t- BuSH or the PTOC carbamate gave a variety of aklaloid skeletons, typically in good to excellent yields, including pyrrolidines, perhydroindoles, pyrrolizidines, tropanes, 9- azabicyclo [4.2. 1] nonanes, 6-azabicyclo [3.2. 1] octanes. 6-Exo and 7-endo cyclizations ...