Elsevier

Tetrahedron Letters

Volume 47, Issue 34, 21 August 2006, Pages 6079-6082
Tetrahedron Letters

First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (−)-epocarbazolin A via Shi epoxidation

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Abstract

Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides a simple route to racemic epocarbazolin A and a non-diastereoselective access to epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of the non-natural (−)-epocarbazolin A.

Graphical abstract

Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides racemic epocarbazolin A and epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of (−)-epocarbazolin A.

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Acknowledgments

We thank the Fonds der Chemischen Industrie for financial support of our project.

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