R. R. Gataullin, K. Yu. Suponitsky, “Unexpected epoxidation product in oxidation of N-tosyl-7-methoxy-1,3a,4,8b-tetrahydrocyclopenta[b]indole with potassium permanganate”, Mendeleev Commun., 2009, Volume 19, Issue 5,Pages 284

This article is cited in 3 papers

Unexpected epoxidation product in oxidation of N-tosyl-7-methoxy-1,3a,4,8b-tetrahydrocyclopenta[b]indole with potassium permanganate

R. R. Gataullin^a, K. Yu. Suponitsky^b

^a Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Abstract: An unexpected product of N-tosyl-7-methoxy-1,3a,4,8b-tetrahydrocyclopenta[b]indole oxidation with potassium permanganate under alkaline conditions was isolated. Along with (2R,3S,3aR,8bS)-N-tosyl-7-methoxy-2,3-dihydroxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole, (3SR,3aRS,8bSR)-N-tosyl-7-methoxy-3-hydroxy-1,2-epoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole was formed.

Keywords: epoxidation reaction, potassium permanganate, X-ray crystallography.

Language: English

DOI: 10.1016/j.mencom.2009.09.019