Synthesis of Benzo-Fused 1-Azabicyclo[m.n.0]alkanes via the Schmidt Reaction:  A Formal Synthesis of Gephyrotoxin

• Published in: Journal of organic chemistry Vol. 65; no. 21; pp. 7158 - 7174
• Main Authors: Pearson, William H, Fang, Wen-kui
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.10.2000; Amer Chemical Soc
• Subjects: Alkaloids - chemical synthesis; Alkanes - chemical synthesis; Amphibian Venoms - chemical synthesis; Aza Compounds - chemical synthesis; Bridged Bicyclo Compounds - chemical synthesis; Chemistry; Chemistry, Organic; Cyclization; Oxidation-Reduction; Physical Sciences; Pyrroles - chemistry; Quinolones - chemistry; Science & Technology; Stereoisomerism; ALCOHOLS; KETONES; ETHERS; ASYMMETRIC-SYNTHESIS; RADICAL CYCLIZATION; CARBONYL-COMPOUNDS; RING-SYSTEM; DART FROGS DENDROBATIDAE; ALKYL AZIDES; ALKALOIDS

The intramolecular capture of benzocyclobutyl, benzocyclopentyl, and benzocyclohexyl carbocations 7 by azides produces spirocyclic aminodiazonium ions 8, which undergo 1,2-C-to-N rearrangement with loss of dinitrogen to produce benzo-fused iminium ions resulting from either aryl (9) or alkyl (10) mi...