4.4 Review

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Journal

CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 43, Issue 1, Pages 130-155

Publisher

SCIENCE PRESS
DOI: 10.6023/cjoc202206035

Keywords

nine-membered N-heterocycles; medium-sized ring compounds; cyclization; cycloaddition; ring expansion

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This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years.
Nine-membered N-heterocycle scaffolds are widely found in natural products and biologically active molecules. The rigid structure of the medium-sized ring plays important roles in the regulation of their biological and pharmacological activities. Therefore, nine- membered N-heterocycle is one of the most attractive medium-sized ring compounds. Because of the increasing entropy and ring extension of nine-membered ring skeleton, the synthesis of nine-membered N-heterocycles is still difficult; especially the effective control of substituent stereoselectivity for the nine-membered ring is one of the greatest challenging topics This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years.

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