Synthesis of helically chiral molecules: stereoselective total synthesis of the perylenequinones phleichrome and calphostin A

RS Coleman, EB Grant

Index: Coleman, Robert S.; Grant, Eugene B. Journal of the American Chemical Society, 1995 , vol. 117, # 44 p. 10889 - 10904

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Citation Number: 71

Abstract

Abstract: The total syntheses of the perylenequinone natural products phleichrome and calphostin A are detailed. The syntheses were based on (1) the de novo construction of regiospecifically oxygenated and selectively protected naphthalene subunits,(2) the enantiospecific introduction of the stereogenic side chains using a chiral (a-alkoxyalky1)- lithium reagent, and (3) a highly atropdiastereoselective Cu (1)-promoted biaryl synthesis ...