Formal synthesis of 6-deoxyerythronolide B |
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Authors: | Crimmins Michael T Slade David J |
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Institution: | Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, USA. crimmins@email.unc.edu |
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Abstract: | reaction: see text] 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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