586390-99-0Relevant articles and documents
Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: Application to the total syntheses of benzastatin E and natural virantmycin
Ori, Mayuko,Toda, Narihiro,Takami, Kazuko,Tago, Keiko,Kogen, Hiroshi
, p. 2075 - 2104 (2007/10/03)
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 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.