TY - JOUR
T1 - Divergent and selective functionalization of 2-formylpyrrole and its application in the total synthesis of the aglycone alkaloid pyrrolemarumine
AU - Martínez-Mora, Eder I.
AU - Caracas, Miguel A.
AU - Escalante, Carlos H.
AU - Madrigal, Damian A.
AU - Quiroz-Florentino, Héctor
AU - Delgado, Francisco
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2016, Sociedad Química de México.
PY - 2016/1/1
Y1 - 2016/1/1
N2 - Diverse 1,2-and 1,2,5-substituted pyrroles were efficiently prepared through a regioselective functionalization of 2-formylpyrrole (5a). This methodology was applied for the first total synthesis of pyrrolemarumine (4b), the aglycone of the corresponding natural pyrrole alkaloid 4”-O-α-L-rhamnopyranoside. The synthesis of 4b was achieved starting from 5a through a seven-step process in 28% overall yield.
AB - Diverse 1,2-and 1,2,5-substituted pyrroles were efficiently prepared through a regioselective functionalization of 2-formylpyrrole (5a). This methodology was applied for the first total synthesis of pyrrolemarumine (4b), the aglycone of the corresponding natural pyrrole alkaloid 4”-O-α-L-rhamnopyranoside. The synthesis of 4b was achieved starting from 5a through a seven-step process in 28% overall yield.
KW - 2-formylpyrrole
KW - Pyrrole alkaloids
KW - Pyrrolemarumine
KW - Vilsmeier-Haack formylation
UR - http://www.scopus.com/inward/record.url?scp=84967341231&partnerID=8YFLogxK
M3 - Artículo
SN - 1870-249X
VL - 60
SP - 23
EP - 33
JO - Journal of the Mexican Chemical Society
JF - Journal of the Mexican Chemical Society
IS - 1
ER -