Abstract

An efficient methodology for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine–CCl 4-mediated stereospecific rearrangement of α,α-disubstituted indoline-2-methanols 15 to 2,2,3-trisubstituted tetrahydroquinolines 26 . The rearrangement precursors 15 are readily prepared by the diastereoselective Grignard addition to 2-acylindolines 13 . The total syntheses of (+)-benzastatin E ( 1 ) and natural virantmycin ( 2a ) were accomplished utilizing this methodology. This rearrangement reaction might afford some chemical precedent for the biogenetic pathway of the benzastatin family.

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