Stereocontrolled epoxidations of cycloheptene derivatives in the palladium-catalyzed route to tropane alkaloids. Total syntheses of scopine and pseudoscopine

…, H Pettersson, JE Baeckvall

Index: Schink, Hans E.; Pettersson, Helena; Baeckvall, Jan-E. Journal of Organic Chemistry, 1991 ,  vol. 56,  # 8  p. 2769 - 2774

Full Text: HTML

Citation Number: 59

Abstract

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 ...