154352-91-7Relevant academic research and scientific papers
Development of a Divergent Synthetic Route to the Erythrina Alkaloids: Asymmetric Syntheses of 8-Oxo-erythrinine, Crystamidine, 8-Oxo-erythraline, and Erythraline
Umihara, Hirotatsu,Yoshino, Tomomi,Shimokawa, Jun,Kitamura, Masato,Fukuyama, Tohru
, p. 6915 - 6918 (2016)
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. Then there were four: The fixed atropisomeric stereochemistry of a medium-sized biaryl intermediate was fully transferred to the central point chirality of a helical intermediate as a result of singlet oxygen oxidation and transannulation. This finding enabled the asymmetric synthesis of a common intermediate, which is amenable to a variety of oxidation-reduction transformations, thus giving rise to the first asymmetric syntheses of four erythrina alkaloids.
Substituted quinol-2-yl-methoxy-phenylacetic acid derivatives
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, (2008/06/13)
Substituted quinol-2-yl-methoxy-phenylacetic acid derivatives are prepared by reacting correspondingly substituted phenols with quinolylmethyl halides or by reacting unsubstituted phenols with quinolylmethyl halides and subsequent alkylation. The substitu
