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Letter

Formal Synthesis of 6-Deoxyerythronolide B

Supporting Info

Michael T. Crimmins* and David J. Slade

Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599

Org. Lett., 2006, 8 (10), pp 2191–2194

DOI: 10.1021/ol0607241

Publication Date (Web): April 15, 2006

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

, crimmins@email.unc.edu

Abstract

The enantioselective synthesis of the carbon skeleton of 6-deoxyerythronolide B has been achieved in 23 linear steps from propionaldehyde. The synthesis relies on an iterative approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish eight of nine stereogenic centers. The remaining stereogenic center at C6 was set through a Myers alkylation employing a complex alkyl iodide.

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Published In Issue May 11, 2006
Received March 24, 2006

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Letter

Formal Synthesis of 6-Deoxyerythronolide B

Abstract

Available Supporting Information for This Article

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History

Recommend & Share

Related Content

General Strategies toward the Syntheses of Macrolide Antibiotics. The Total Syntheses of 6-Deoxyerythronolide B and Oleandolide

Macrolactonization via Hydrocarbon Oxidation

Pseudoephedrine as a Practical Chiral Auxiliary for the Synthesis of Highly Enantiomerically Enriched Carboxylic Acids, Alcohols, Aldehydes, and Ketones

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