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

Only nine steps away: PPh3/CCl4‐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 step...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-06, Vol.42 (22), p.2540-2543
Main Authors: Ori, Mayuko, Toda, Narihiro, Takami, Kazuko, Tago, Keiko, Kogen, Hiroshi
Format: Article
Language:English
Subjects:
alkaloids
Antiviral Agents - chemical synthesis
Antiviral Agents - chemistry
Indoles - chemistry
Methanol - chemistry
Models, Molecular
Molecular Structure
natural products
Quinolines - chemical synthesis
Quinolines - chemistry
rearrangement
Stereoisomerism
total synthesis
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Summary:Only nine steps away: PPh3/CCl4‐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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351069