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A Concise, Biomimetic Total Synthesis of Stephacidin A and Notoamide B

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  • We are grateful to the National Institutes of Health for financial support (CA70375). Mass Spectra were obtained on instruments supported by the NIH Shared Instrument Grant GM49631. We are grateful to Dr. S. Tsukamoto of Kanazawa University for kindly providing NMR spectra of stephacidin A and notoamide B. We thank Kyowa Hakko Kogyo Co., Ltd. for providing us with a sample of cis-3-hydroxy-L-proline. We are grateful to Prof. R. L. Funk of Penn. State University for useful discussions.

Abstract

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Copying nature: A biomimetic total synthesis of stephacidin A has been accomplished using an intramolecular Diels–Alder reaction. Stephacidin A was then converted into notoamide B in a single step by oxaziridine-mediated oxidation to provide the first biomimetic total synthesis of notoamide B (see scheme).

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