Asymmetric total syntheses of (−)-variabilin and (−)-glycinol

MA Calter, N Li

Index: Calter, Michael A.; Li, Na Organic Letters, 2011 , vol. 13, # 14 p. 3686 - 3689

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Citation Number: 25

Abstract

Total syntheses of (−)-variabilin and (−)-glycinol have been accomplished, using the catalytic, asymmetric “interrupted” Feist–Bénary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald–Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.