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Total Syntheses of (−)-Scabronines G and A, and (−)-Episcabronine A

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  • This work was financially supported in part by the Grant-in-Aid for Scientific Research on Innovative Areas. 2105 Organic Synthesis Based on Reaction Integration: Development of New Methods and Creation of New Substances and for Scientific Research (B) (25293003) by the MEXT, and a Waseda University Grant for Special Research Projects. We are grateful to Prof. T. Ohta (Kanazawa University) for sending us copies of 1H and 13C NMR spectra. The fellowship for young scientists to Y.K. from JSPS (5515) is also gratefully acknowledged.

Abstract

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Making scab(ronine)s: The total synthesis of (−)-scabronine G features a highly stereoselective oxidative dearomatization/intramolecular inverse-electron-demand Diels–Alder reaction cascade, and the first total synthesis of (−)-scabronine A comprises a highly stereoselective oxa-Michael/protonation/acetalization cascade. The first total synthesis of (−)-episcabronine A includes another highly stereoselective cascade.

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