Issue 91, 2018

Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines

Abstract

An expedient route to the pentacyclic core of the tryptoquivaline alkaloids and the total synthesis of natural product (+)-3′-(4-oxoquinazolin-3-yl)spiro[1H-indole-3,5′-oxolane]-2,2′-dione (1) have been achieved. The route is enabled by a key, highly stereoselective, aldol reaction catalysed by a Ag(I) and cinchona-derived aminophosphine ligand system, forming a highly substituted oxazoline ring, and setting the C1 spirocyclic stereocentre for downstream manipulation.

Graphical abstract: Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines

Supplementary files

Article information

Article type
Communication
Submitted
14 Sep 2018
Accepted
12 Oct 2018
First published
15 Oct 2018

Chem. Commun., 2018,54, 12860-12862

Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines

T. Wei and D. J. Dixon, Chem. Commun., 2018, 54, 12860 DOI: 10.1039/C8CC07479H

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