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Total Synthesis of Crocagin A
Author(s) -
Bihelovic Filip,
Stichnoth Desiree,
Surup Frank,
Müller Rolf,
Trauner Dirk
Publication year - 2017
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.201612641
Subject(s) - total synthesis , natural product , stereoselectivity , reductive amination , electrophile , amination , electrophilic amination , chemistry , combinatorial chemistry , stereochemistry , double bond , organic chemistry , catalysis
Abstract Crocagin A ( 1 ) combines an attractive molecular structure with an unusual biosynthesis and bioactivity. An efficient synthesis of crocagin A is presented that hinges on an early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond. This synthesis confirms the absolute configuration of crocagin A and provides access to the natural product and derivatives thereof for further biological testing.