Stereocontrolled synthesis of (-)-galanthamine

V Satcharoen, NJ McLean, SC Kemp, NP Camp…

Index: Satcharoen, Vachiraporn; McLean, Neville J.; Kemp, Stephen C.; Camp, Nicholas P.; Brown, Richard C. D. Organic Letters, 2007 , vol. 9, # 10 p. 1867 - 1869

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Citation Number: 61

Abstract

An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically ...