Efficient Asymmetric Synthesis of Pumiliotoxin C via Intramolecular [4+ 2] Cycloaddition
W Oppolzer, E Flaskamp, LW Bieber
Index: Oppolzer, Wolfgang; Flaskamp, Elmar; Bieber, Lothar W. Helvetica Chimica Acta, 2001 , vol. 84, # 1 p. 141 - 145
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Citation Number: 47
Abstract
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 ...
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