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Helvetica Chimica Acta

Efficient Asymmetric Synthesis of Pumiliotoxin C via Intramolecular [4+ 2] Cycloaddition

W Oppolzer, E Flaskamp, LW Bieber

文献索引:Oppolzer, Wolfgang; Flaskamp, Elmar; Bieber, Lothar W. Helvetica Chimica Acta, 2001 , vol. 84, # 1 p. 141 - 145

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被引用次数: 47

摘要

Abstract An efficient asymmetric synthesis in nine steps of natural (−)-pumiliotoxin C (1), a decahydroquinoline alkaloid found in the skin of Central American frog species, is presented. The enantiomerically pure starting material (S)-norvalinol (3), obtained from commercial (S)-norvaline, was cyclized in a one-pot procedure to the tosylated aziridine 5. Ring opening with propargylmagnesium bromide led to the acetylenic sulfonamide ...