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

ABSTRACT: Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Be?nary 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

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

Calter Michael A MA Li Na N

Organic letters 20110613 14

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. ...[more]

PMID: 21667928

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