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Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B.

ABSTRACT: The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.

SUBMITTER: Su S

PROVIDER: S-EPMC3164937 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B.

Su Shun S Rodriguez Rodrigo A RA Baran Phil S PS

Journal of the American Chemical Society 20110816 35

The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH( ...[more]

PMID: 21846138

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