Journal of natural products

Enantioselective Total Synthesis and X-ray Structures of the Tetrahydroprotoberberine Alkaloids (−)-(S)-Tetrahydropalmatrubine and (−)-(S)-Corytenchine

AL Zein, LN Dawe, PE Georghiou

Index: Zein, Ahmed L.; Dawe, Louise N.; Georghiou, Paris E. Journal of Natural Products, 2010 , vol. 73, # 8 p. 1427 - 1430

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Citation Number: 10

Abstract

Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N- norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (> 95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler− Napieralski cyclization/reduction approach.