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Development of a Divergent Synthetic Route to the Erythrina Alkaloids: Asymmetric Syntheses of 8‐Oxo‐erythrinine, Crystamidine, 8‐Oxo‐erythraline, and Erythraline
Author(s) -
Umihara Hirotatsu,
Yoshino Tomomi,
Shimokawa Jun,
Kitamura Masato,
Fukuyama Tohru
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602650
Subject(s) - erythrina , moiety , chemistry , stereospecificity , singlet oxygen , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , oxygen , catalysis , medicine , traditional medicine
A general synthetic methodology toward the erythrina alkaloids has been developed. Inspired by a proposed biosynthetic mechanism, the medium‐sized chiral biaryl lactam was asymmetrically transformed into the common core A–D rings by a stereospecific singlet oxygen oxidation of the phenol moiety, followed by a transannular aza‐Michael reaction to the dienone functionality. The late‐stage manipulation of the oxidation and oxygenation states of the functional groups on the peripheral moieties enabled the flexible syntheses of the erythrina alkaloids.