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Synthesis of the C21-C34 fragment of antascomicin B.

ABSTRACT: The C21-C34 fragment of the potent FKBP12-binding macrolide antascomicin B was prepared using Ireland-Claisen and allylic diazene rearrangements to establish the C26/C27 and the C23 stereocenters, respectively. Directed hydrogenation installed the C29 ?-configuration. The fragment possesses 7 of the 11 fixed stereocenters contained in the natural product.

SUBMITTER: Hutchison JM 

PROVIDER: S-EPMC3244276 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Synthesis of the C21-C34 fragment of antascomicin B.

Hutchison John M JM   Gibson Andrew S AS   Williams David T DT   McIntosh Matthias C MC  

Tetrahedron letters 20111001 48

The C21-C34 fragment of the potent FKBP12-binding macrolide antascomicin B was prepared using Ireland-Claisen and allylic diazene rearrangements to establish the C26/C27 and the C23 stereocenters, respectively. Directed hydrogenation installed the C29 β-configuration. The fragment possesses 7 of the 11 fixed stereocenters contained in the natural product. ...[more]

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