A one-pot bicycloannulation method for the synthesis of tetrahydroisoquinoline systems

A Padwa, LS Beall, TM Heidelbaugh…

Index: Padwa, Albert; Beall, L. Scott; Heidelbaugh, Todd M.; Liu, Bing; Sheehan, Scott M. Journal of Organic Chemistry, 2000 , vol. 65, # 9 p. 2684 - 2695

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Citation Number: 71

Abstract

A highly effective method for the synthesis of the core indolo [2, 3-a] quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomünchnones as transient 1, 3-dipoles that undergo ready intramolecular cycloaddition across the tethered π-bond to give thio- bicycloannulated products in a one-pot operation. The stereochemical outcome of the ...