Enantioselective Construction of Vicinal Stereogenic Quaternary Centers by Dialkylation: Practical Total Syntheses of (+)- andmeso-Chimonanthine
- 3 January 2000
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 39 (1) , 213-215
- https://doi.org/10.1002/(sici)1521-3773(20000103)39:1<213::aid-anie213>3.0.co;2-z
Abstract
All three stereoisomers of the hexacyclic 3a,3a′-bispyrrolidino[2,3-b]indoline moiety found in complex indole alkaloids can be prepared, as illustrated by total syntheses of meso-chimonanthine (1) and (+)-chimonanthine (2). A rare example of high diastereoselectivity arising from the combination of a prostereogenic enolate with a chiral electrophile containing a sp3 carbon atom is the key feature of the asymmetric synthesis of the C2 stereoisomer.This publication has 0 references indexed in Scilit: