Tetrahedron

An efficient synthesis of magallanesine using [1, 2]-Meisenheimer rearrangement and Heck cyclization

…, Y Sakamoto, Y Oketo, S Harusawa, T Kurihara

Index: Yoneda, Ryuji; Sakamoto, Yasuhiko; Oketo, Yoshifumi; Harusawa, Shinya; Kurihara, Takushi Tetrahedron, 1996 , vol. 52, # 46 p. 14563 - 14576

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Citation Number: 26

Abstract

A straightforward total synthesis of magallanesine 1 was accomplished from readily available isoquinolineacetate 14. This synthesis is emphasized by the following two points; i. the [1, 2]-Meisenheimer rearrangement of the azetidine N-oxide 22 for the preparation of azocine ring, ii. the Pd-catalyzed intramolecular Heck reaction of N-benzoylenaminone 38 for the construction of isoindoloazocine skeleton.