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Total Synthesis of the Marine Alkaloid Discoipyrrole C via the MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole

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Date

2017-11-28

Authors

Yan, Qiao
Ma, Xiang
Banwell, Martin
Ward, Jas

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

A total synthesis of the marine alkaloid discoipyrrole C (3) is described. In the pivotal step, the 2,3,5-trisubstituted pyrrole 19 was treated with MoOPH in the presence of MeOH, and the resulting methoxylated 1,2-dihydro-3H-pyrrol-3-one 20 subjected to reaction with potassium carbonate in MeOH then trifluoroacetic acid and H2O. This gave a mixture of target 3 and its dehydration product, and the structure of the former compound was confirmed by single-crystal X-ray analysis.

Description

Keywords

marine alkaloid discoipyrrole C (3), 2,3,5-trisubstituted pyrrole 19, MoOPH, MeOH

Citation

URI

http://hdl.handle.net/1885/159362

Collections

ANU Research Publications

Source

Journal of Natural Products

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/acs.jnatprod.7b00872

Restricted until

2037-12-31

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01_Yan_Total_Synthesis_of_the_Marine_2017.pdf (1.29 MB)

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