Stereospecific Construction of Contiguous Quaternary and Tertiary Stereocenters by Rearrangement from Indoline??2??methanol to 2, 2, 3??Trisubstituted …

M Ori, N Toda, K Takami, K Tago…

Index: Ori, Mayuko; Toda, Narihiro; Takami, Kazuko; Tago, Keiko; Kogen, Hiroshi Angewandte Chemie - International Edition, 2003 , vol. 42, # 22 p. 2540 - 2543

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Citation Number: 36

Abstract

D= À15. 0 (c= 0.84 in CHCl3)(ref.[16, 20][a] 18 D= À11. 1 (c= 0.175 in CHCl3))]. This synthesis required only nine steps from indoline 8. In summary, we have developed a novel synthesis of chiral trisubustituted tetrahydroquinolines in which contiguous quaternary and tertiary stereogenic centers are constructed in analogy to the hypothetical biosynthetic pathway. The reaction was applied to the first total synthesis of natural virantmycin in only ...