General strategy for the construction of enantiopure pyrrolidine-based alkaloids. Total synthesis of (-)-monomorine.
An enantiopure cis-2,5-disubstituted pyrrolidine building block was prepared from cocaine. The synthetic utility of this compound as a chiral building block was demonstrated by a short and efficient synthesis of the pyrrolidine-based alkaloid (-)-monomorine (six steps, 37% overall yield).
Zhang
Suhong
S
Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.
Xu
Liang
L
Miao
Lei
L
Shu
Hong
H
Trudell
Mark L
ML
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; D011759:Pyrrolidines; C110223:indolizidine-195B; C032519:pyrrolidine