Premium
A Desymmetrization‐Based Total Synthesis of Reserpine
Author(s) -
Park Jisook,
Chen David Y.K.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810974
Subject(s) - desymmetrization , reserpine , chemistry , pharmacology , organic chemistry , medicine , catalysis , enantioselective synthesis
Reported herein is a desymmetrization‐based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E‐ring precursor, in contrast to the synthesis‐intensive and stereodefined E‐ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.