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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612641
Subject(s) - total synthesis , natural product , chemistry , reductive amination , stereoselectivity , electrophile , amination , electrophilic amination , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.