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Formal synthesis of 6-deoxyerythronolide B.

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.

SUBMITTER: Crimmins MT 

PROVIDER: S-EPMC2546576 | biostudies-literature | 2006 May

REPOSITORIES: biostudies-literature

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Formal synthesis of 6-deoxyerythronolide B.

Crimmins Michael T MT   Slade David J DJ  

Organic letters 20060501 10

[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. ...[more]