Journal article

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.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Wei, T., & Dixon, D. (2018). Catalytic stereoselective total synthesis of a spiro-oxindole alkaloid and the pentacyclic core of tryptoquivalines. Chemical Communications, 54(91), 12860–12862.

MLA Style

Wei, T., and D. Dixon. “Catalytic Stereoselective Total Synthesis of a Spiro-Oxindole Alkaloid and the Pentacyclic Core of Tryptoquivalines.” Chemical Communications, vol. 54, no. 91, Royal Society of Chemistry, 2018, pp. 12860–62.

Chicago Style

Wei, T, and D Dixon. 2018. “Catalytic Stereoselective Total Synthesis of a Spiro-Oxindole Alkaloid and the Pentacyclic Core of Tryptoquivalines.” Chemical Communications 54 (91): 12860–62.
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Files:: Dixon_CC_tryptoquivaline_acceptedmanuscript.pdf

(Preview, Accepted manuscript, pdf, 906.7KB, Terms of use)

Publisher copy:: 10.1039/c8cc07479h

Authors

+ Wei, T More by this author

Institution:: University of Oxford
Division:: MPLS Division
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Corpus Christi College
Role:: Author

+ Dixon, D More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Wadham College
Role:: Author

Publisher:: Royal Society of Chemistry
Journal:: Chemical Communications More from this journal
Volume:: 54
Issue:: 91
Pages:: 12860-12862
Publication date:: 2018-10-15
Acceptance date:: 2018-10-12
DOI:: 10.1039/c8cc07479h
EISSN:: 1364-548X
ISSN:: 1359-7345
Pmid:: 30375595

Language:: English
Pubs id:: pubs:936554
UUID:: uuid:5a615baf-0b39-42bb-9655-8ab018a53f59
Local pid:: pubs:936554
Source identifiers:: 936554
Deposit date:: 2018-12-18

Terms of use

Copyright holder:: The Royal Society of Chemistry
Copyright date:: 2018
Notes:: This journal is © The Royal Society of Chemistry 2018. This is the accepted manuscript version of the article. The final version is available online from The Royal Society of Chemistry at: https://doi.org/10.1039/c8cc07479h

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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