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The Enantioselective Total Synthesis of Exochomine
Author(s) -
Gao Alison X.,
Hamada Tomoaki,
Snyder Scott A.
Publication year - 2016
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.201604744
Subject(s) - enantioselective synthesis , context (archaeology) , combinatorial chemistry , computer science , molecule , construct (python library) , chemistry , organic chemistry , catalysis , programming language , paleontology , biology
Abstract Molecules that possess fully substituted chiral centers are often challenging to construct, particularly if those centers connect two seemingly different halves or include a nitrogen atom. Herein, we describe an efficient approach to a molecule that combines both challenges in a single center in the form of exochomine. Failures in direct coupling led to a design fueled by highly specific reaction conditions for several steps and the development of an improved protocol for 1,4‐reduction in a hindered context where numerous side reactions were possible. These chemoselective solutions should have value to other problems. Challenges in obtaining matching spectral data for the synthesized natural product are also discussed.