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Unified enantioselective total syntheses of (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine and (−)-mersicarpine

Author:
Liu, Yao, Wang, Honggen
Source:
Chemical communications 2019 v.55 no.24 pp. 3544-3547
ISSN:
1364-548X
Subject:
alkaloids, alkylation, catalytic activity, enantioselectivity, palladium
Abstract:
A unified strategy enabled the enantioselective syntheses of (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine and (−)-mersicarpine from a common 2-alkylated indole intermediate bearing an all-carbon quaternary stereogenic center. The Smith-modified Madelung indole synthesis was used to couple simple o-toluidine with chiral lactone (+)-8, incorporating the key elements for further cyclizations. Lactone (+)-8 was prepared via a palladium-catalyzed intermolecular asymmetric allylic alkylation. The unified and protecting-group-free reaction sequences allowed the synthesis of these alkaloids in a maximum of 10 steps and with high efficiency.
Agid:
6332109