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Synthesis of Each Enantiomer of Rocaglamide by Means of a Palladium(0)‐Catalyzed Nazarov‐Type Cyclization
Author(s) -
Zhou Zhe,
Tius Marcus A.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501374
Subject(s) - stereocenter , chemistry , stereochemistry , total synthesis , catalysis , enantiomer , enantioselective synthesis , reagent , palladium , combinatorial chemistry , organic chemistry
Abstract A recently reported Pd 0 ‐catalyzed asymmetric Nazarov‐type cyclization has been successfully applied in the key step of the first catalytic asymmetric total synthesis of (−)‐rocaglamide (natural) and (+)‐rocaglamide. The stereochemistry at the C3 position that controls the stereochemistry of all other stereocenters is determined in the cyclization step. This versatile and modular synthesis proceeds from simple reagents.