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

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.

SUBMITTER: Calter MA 

PROVIDER: S-EPMC3132817 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature