Total Syntheses of (−)-Scabronines G and A, and (−)-Episcabronine A†
Yu Kobayakawa
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/
Search for more papers by this authorCorresponding Author
Prof. Masahisa Nakada
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/Search for more papers by this authorYu Kobayakawa
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/
Search for more papers by this authorCorresponding Author
Prof. Masahisa Nakada
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/
Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555 (Japan) http://www.chem.waseda.ac.jp/nakada/Search for more papers by this authorThis 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.
Graphical Abstract
Eine hoch stereoselektive Reaktionskaskade aus oxidativer Desaromatisierung und intramolekularer Diels-Alder-Reaktion mit inversem Elektronenbedarf steht im Mittelpunkt einer Totalsynthese von (−)-Scabronin G, während die erste Totalsynthese von (−)-Scabronin A auf einer hoch stereoselektiven Kaskade aus Oxa-Michael-Reaktion, Protonierung und Acetalisierung beruht. Bei der ersten Totalsynthese von (−)-Episcabronin A wurde analog verfahren.
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