Organic letters

A torquoselective 6π electrocyclization approach to reserpine alkaloids

GA Barcan, A Patel, KN Houk, O Kwon

Index: Barcan, Gregg A.; Patel, Ashay; Houk; Kwon, Ohyun Organic Letters, 2012 , vol. 14, # 21 p. 5388 - 5391

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Citation Number: 20

Abstract

A highly torquoselective thermal triene 6π electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo [2, 3-a] benzo [g] quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross- coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen ...

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