Spirodiepoxides in Total Synthesis:  Epoxomicin

Sreenivas Katukojvala, Kristin N. Barlett, Stephen D. Lotesta, and Lawrence J. Williams*
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854
J. Am. Chem. Soc., 2004, 126 (47), pp 15348–15349
DOI: 10.1021/ja044563c
Publication Date (Web): November 4, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ljw@rutchem.rutgers.edu

Abstract

Abstract Image

The first use of the spirodiepoxide functional group in total synthesis, a study culminating in an efficient synthesis of the potent proteasome inhibitor epoxomicin, is described. Spirodiepoxides derived from allenes by oxidation are shown to give syn disubstituted ketones and their derivatives, including ortho ester, oxazoline, azido epoxide, as well as sulfonamide-, amide-, and azide-containing hydroxy ketones.

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History

  • Published In Issue December 01, 2004
  • Received September 8, 2004

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