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

Qiao Yan; Xiang Ma; Martin G. Banwell; Jas S. Ward

doi:10.1021/acs.jnatprod.7b00872

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

Qiao Yan
, Xiang Ma
, Martin G. Banwell^*
, Jas S. Ward

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

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 H ₂ O. 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.

Original language	English
Pages (from-to)	3305-3313
Number of pages	9
Journal	Journal of Natural Products
Volume	80
Issue number	12
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00872
Publication status	Published - 22 Dec 2017

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

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 H 2 O. 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.",

author = "Qiao Yan and Xiang Ma and Banwell, \{Martin G.\} and Ward, \{Jas S.\}",

note = "Publisher Copyright: {\textcopyright} 2017 The American Chemical Society and American Society of Pharmacognosy.",

year = "2017",

month = dec,

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doi = "10.1021/acs.jnatprod.7b00872",

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T1 - Total Synthesis of the Marine Alkaloid Discoipyrrole C via the MoOPH-Mediated Oxidation of a 2,3,5-Trisubstituted Pyrrole

AU - Yan, Qiao

AU - Ma, Xiang

AU - Banwell, Martin G.

AU - Ward, Jas S.

PY - 2017/12/22

Y1 - 2017/12/22

N2 - 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 H 2 O. 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.

AB - 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 H 2 O. 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.

UR - https://www.scopus.com/pages/publications/85039152248

U2 - 10.1021/acs.jnatprod.7b00872

DO - 10.1021/acs.jnatprod.7b00872

M3 - Article

SN - 0163-3864

VL - 80

SP - 3305

EP - 3313

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 12

ER -

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

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