Tetrahedron

Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A

T Kan, A Fujiwara, H Kobayashi, T Fukuyama

Index: Kan, Toshiyuki; Fujiwara, Akiko; Kobayashi, Hideki; Fukuyama, Tohru Tetrahedron, 2002 , vol. 58, # 32 p. 6267 - 6276

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Citation Number: 40

Abstract

Synthesis of medium-and large-sized cyclic amines using alkylation with 2- nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A (9), an 18-membered cyclic polyamine.