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

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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

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Publication details

The article was received on 14 Sep 2018, accepted on 12 Oct 2018 and first published on 15 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07479H
Citation: Chem. Commun., 2018, Advance Article
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    Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines

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

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