Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements

Wei Qi; Matthias C McIntosh

doi:10.1016/j.tet.2008.05.070

Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements

Tetrahedron. 2008;64(29):7021-7025. doi: 10.1016/j.tet.2008.05.070.

Authors

Wei Qi¹, Matthias C McIntosh

Affiliation

¹ Dept. of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701.

Abstract

The C22-C34 fragment of antascomicin B lacking the C31 and C32 hydroxyl groups has been prepared in 11 steps from commercially available 2-OH-cyclohexanone. An Ireland-Claisen rearrangement was employed to install the C26 and C27 stereocenters. Our recently reported diastereoselective acyclic 1,3-reductive transposition was used to establish the remote C23 stereocenter. Directed hydrogenation was employed to set the C29 stereocenter. The model compound contains 5 of the stereocenters and all of the carbons of the corresponding fragment of antascomicin B.

Abstract

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