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Stereospecific Construction of Contiguous Quaternary and Tertiary Stereocenters by Rearrangement from Indoline‐2‐methanol to 2,2,3‐Trisubstituted Tetrahydroquinoline: Application to an Efficient Total Synthesis of Natural Virantmycin
Author(s) -
Ori Mayuko,
Toda Narihiro,
Takami Kazuko,
Tago Keiko,
Kogen Hiroshi
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351069
Subject(s) - stereocenter , indoline , stereospecificity , methanol , total synthesis , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
Only nine steps away : PPh 3 /CCl 4 ‐mediated stereospecific rearrangement of α,α‐disubstituted indoline‐2‐methanol to 2,2,3‐trisubstituted optically active tetrahydroquinoline (see scheme) has been developed. The reaction was applied to the first total synthesis of natural virantmycin, in only nine steps from commercially available starting material.