TY - JOUR
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.
N1 - Publisher Copyright:
© 2017 The American Chemical Society and American Society of Pharmacognosy.
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 - http://www.scopus.com/inward/record.url?scp=85039152248&partnerID=8YFLogxK
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 -