American Chemical Society
ol4c00491_si_001.pdf (2.36 MB)

Synthesis of the Cyclopentane Core Skeleton of Cranomycin and Jogyamycin

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journal contribution
posted on 2024-04-03, 12:04 authored by Shuo Du, Xing Huo, Xiaolei Wang
Cranomycin and jogyamycin, two aminocyclopentitol natural products, possess complex structures and potential medicinal properties. This review describes synthetic studies about the process of making an advanced intermediate of cranomycin and jogyamycin. This highly functionalized intermediate, featuring three contiguous amine-substituted stereocenters, was constructed from cyclopentadiene through a series of reactions including the nitroso Diels–Alder reaction, nitrogen radical cyclization reaction, 1,2-nitrogen migration, and stereoselective nitrogen addition.