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Letter

Formal Synthesis of 6-Deoxyerythronolide B

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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

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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Recommend & Share

Related Content

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

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