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A Desymmetrization‐Based Total Synthesis of Reserpine
Author(s) -
Park Jisook,
Chen David Y.K.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810974
Subject(s) - desymmetrization , reserpine , chemistry , ring (chemistry) , total synthesis , stereochemistry , indole test , reagent , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , biology , pharmacology
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.