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An allenic Pauson-Khand approach to 6,12-guaianolides.

ABSTRACT: Cyclocarbonylation of ?-methylene butyrolactone-containing allene-ynes affords 6,12-guaianolide ring systems. Incorporation of the ?-methylene butyrolactone early in a synthetic sequence is rare for reactivity reasons; however, this moiety proves to be beneficial to the allenic Pauson-Khand reaction. The three double bonds and the ketone in the resulting 5-7-5 ring system bear significant differences in their reactivity and are ideally positioned for synthetic application to 6,12-guaianolides and analogs.

SUBMITTER: Grillet F

PROVIDER: S-EPMC3258445 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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An allenic Pauson-Khand approach to 6,12-guaianolides.

Grillet Francois F Huang Chaofeng C Brummond Kay M KM

Organic letters 20111109 23

Cyclocarbonylation of α-methylene butyrolactone-containing allene-ynes affords 6,12-guaianolide ring systems. Incorporation of the α-methylene butyrolactone early in a synthetic sequence is rare for reactivity reasons; however, this moiety proves to be beneficial to the allenic Pauson-Khand reaction. The three double bonds and the ketone in the resulting 5-7-5 ring system bear significant differences in their reactivity and are ideally positioned for synthetic application to 6,12-guaianolides an ...[more]

PMID: 22070869

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