115522-45-7Relevant academic research and scientific papers
Stereocontrolled Epoxidations of Cycloheptene Derivatives in the Palladium-Catalyzed Route to Tropane Alkaloids. Total Syntheses of Scopine and Pseudoscopine
Schink, Hans E.,Pettersson, Helena,Baeckvall, Jan-E.
, p. 2769 - 2774 (2007/10/02)
Stereoselective total syntheses of the tropane alkaloids scopine (1) and pseudoscopine (3) have been developed via the chloroacetoxylation approach.Palladium-catalyzed 1,4-chloroacetoxylation of diene 6 afforded the key intermediate 7.Subsequent substitution of the allylic chloride by TsNH- with either retention (Pd(0) catalysis) or inversion (SN2) of configuration gave 10 and 16, respectively.The epoxy oxygen was introduced syn to the nitrogen function prior to cyclization by utilizing the syn-directive effect of the allylic sulfonamido group in the epoxidation.Cyclization of the epoxides 12 and 21, followed by replacement of the tosyl group by a methyl group and subsequent debenzylation, afforded the title compounds 1 and 3, respectively.
STEREOCONTROLLED SYNTHESIS OF TROPANOL DERIVATIVES VIA PALLADIUM-CATALYZED REACTIONS
Baeckvall, J. E.,Renko, Z. D.,Bystroem, S. E.
, p. 4199 - 4202 (2007/10/02)
A general method for the transformation of 1,3-cycloheptadienes to tropane alkaloid derivatives was developed.The procedure was applied to the stereocontrolled synthesis of the exo- and endo-tropanol derivatives 1 and 2.The approach is based on a dual stereocontrol in the 1,4-functionalization of conjugated dienes.
