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A general route toward the synthesis of the cladiellin skeleton utilizing a SmI2-mediated cyclization.

ABSTRACT: An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI(2)-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2505338 | biostudies-literature | 2006 Feb

REPOSITORIES: biostudies-literature

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A general route toward the synthesis of the cladiellin skeleton utilizing a SmI2-mediated cyclization.

Molander Gary A GA Czakó Barbara B St Jean David J DJ

The Journal of organic chemistry 20060201 3

An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI(2)-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer o ...[more]

PMID: 16438535

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