An efficient approach toward pyrrolidinyllactone system characteristic of the Stemona alkaloids. Lewis acid catalyzed stereoselective reaction of N-benzyloxycarbonyl- …

Y Morimoto, K Nishida, Y Hayashi, H Shirahama

Index: Morimoto; Nishida; Hayashi; Shirahama Tetrahedron Letters, 1993 , vol. 34, # 36 p. 5773 - 5776

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Citation Number: 58

Abstract

Abstract Pyrrolidinyllactone system 7, common partial structure presented in most Stemona alkaloids, was stereoselectively prepared by two-step sequence: i) syn-selective condensation of N-benzyloxycarbonyl-2-methoxypyrrolidine (8) with 3-methyl-2- trimethylsilyloxyfuran (9) catalyzed by Lewis acids; ii) diastereoselective hydrogenation of the product 10 (NaBH 4, NiCl 2/MeOH).