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Letter

Asymmetric [4 + 3] Cycloadditions between Benzofuranyldiazoacetates and Dienes: Formal Synthesis of (+)-Frondosin B

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Jeremy P. Olson and Huw M. L. Davies*

Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000

Org. Lett., 2008, 10 (4), pp 573–576

DOI: 10.1021/ol702844g

Publication Date (Web): January 24, 2008

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, hdavies@acsu.buffalo.edu

Abstract

The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh₂(R-DOSP)₄, generates formal [4 + 3] cycloadducts with >94% de and 91−98% ee. The reaction proceeds by a tandem cyclopropanation/Cope rearrangement followed by a stereoselective tautomerization. This methodology was extended to a formal synthesis of (+)-frondosin B.

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Published In Issue February 21, 2008
Received November 24, 2007

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Letter

Asymmetric [4 + 3] Cycloadditions between Benzofuranyldiazoacetates and Dienes: Formal Synthesis of (+)-Frondosin B

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition

Total Synthesis of (−)-Acutumine

Enantioselective Total Synthesis of (−)-Napyradiomycin A1 via Asymmetric Chlorination of an Isolated Olefin

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