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The Miharamycins and Amipurimycin: their Structural Revision and the Total Synthesis of the Latter
Author(s) -
Wang Shengyang,
Zhang Qingju,
Zhao Yachen,
Sun Jiansong,
Kang Wenjia,
Wang Fei,
Pan Haixue,
Tang Gongli,
Yu Biao
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905723
Subject(s) - nonane , diffraction , stereochemistry , chemistry , crystallography , physics , optics
The structural puzzle of amipurimycin, a peptidyl nucleoside antibiotic, is solved by total synthesis and X‐ray diffraction analysis, with the originally proposed configurations at C3′ and C8′ inverted and those at C6′, C2′′, and C3′′ corrected. A similar structural revision of the relevant miharamycins is proposed via chemical transformations and then validated by X‐ray diffraction analysis. The miharamycins bear an unusual trans ‐fused dioxabicyclo[4.3.0]nonane sugar scaffold, which was previously assigned as being in the cis configuration.