Total synthesis of phenanthroindolizidine alkaloids via asymmetric deprotonation of N-Boc-pyrrolidine†
Meng Deng,Bo Su,Hui Zhang,Yuxiu Liu,Qingmin Wang
RSC Advances Pub Date : 01/28/2014 00:00:00 , DOI:10.1039/C3RA47465H
Abstract

A concise and efficient enantioselective strategy to synthesize two typical phenanthroindolizidine alkaloids, 14-hydroxyantofine and antofine, was developed, featuring an asymmetric deprotonation/diastereoselective carbonyl addition sequence during which the formation of a chiral C-13a center and connection of pyrrolidine and phenanthrene moieties were achieved efficiently in one step. The absolute configuration of the C-13a stereocenter can be delicately controlled by using different enantiomers of sparteine, both of which are commercially available.

Graphical abstract: Total synthesis of phenanthroindolizidine alkaloids via asymmetric deprotonation of N-Boc-pyrrolidine