Stereospecific synthesis of 2, 2, 3-trisubstituted tetrahydroquinolines: application to the total syntheses of benzastatin E and natural virantmycin

M Ori, N Toda, K Takami, K Tago, H Kogen

Index: Ori, Mayuko; Toda, Narihiro; Takami, Kazuko; Tago, Keiko; Kogen, Hiroshi Tetrahedron, 2005 , vol. 61, # 8 p. 2075 - 2104

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Citation Number: 33

Abstract

An efficient methodology for the synthesis of 2, 2, 3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine–CCl4-mediated stereospecific rearrangement of α, α-disubstituted indoline-2-methanols to 2, 2, 3-trisubstituted tetrahydroquinolines. The rearrangement precursors are readily prepared by the diastereoselective Grignard addition to 2-acylindolines. The total syntheses of (+)- ...