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Asymmetric Synthesis of Fortucine and Reassignment of Its Absolute Configuration
Author(s) -
Beaulieu MarcAndré,
Ottenwaelder Xavier,
Canesi Sylvain
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402323
Subject(s) - hypervalent molecule , absolute configuration , enantioselective synthesis , total synthesis , natural product , reagent , iodine , absolute (philosophy) , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , philosophy , epistemology
A convergent and enantioselective synthesis of fortucine was achieved from the starting materials tyrosine methyl ester and 3‐hydroxy‐4‐methoxybenzaldehyde. The synthesis is based on two key steps mediated by a hypervalent iodine reagent. This work has enabled us to reassign the absolute configuration of the natural product reported in the literature.