Organic Letters
Organic Letters
5 years ago

Asymmetric Total Synthesis of Eburnamine and Eucophylline: A Biomimetic Attempt for the Total Synthesis of Leucophyllidine

Asymmetric Total Synthesis of Eburnamine and Eucophylline: A Biomimetic Attempt for the Total Synthesis of Leucophyllidine
Akash Mishra, Ganesh Pandey, Jagadish Khamrai
The first enantiospecific total synthesis of (+)-6 has been achieved employing a Friedländer quinoline synthesis as a key step. Asymmetric synthesis of the architecturally complex eburnamine 5 has also been accomplished utilizing an intramolecular acid-mediated cyclization of a carbinol amine lactone moiety. Highlights of the effective modular synthetic strategy include development of the common precursor 4 for the construction of the privileged scaffolds 5 and 6 with an all-carbon quaternary stereocenter utilizing a Johnson–Claisen rearrangement strategy. Attempts have been made to synthesize 1 by the biomimetic coupling of 5 and (+)-6; however, regioisomeric 26 was formed.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01410

DOI: 10.1021/acs.orglett.7b01410

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