An Expeditious Total Synthesis of 5′-Deoxy-toyocamycin and 5′-Deoxysangivamycin

In present paper, an expeditious total synthesis of naturally occurring 5&#8242;-deoxytoyocamycin and 5&#8242;-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at <i>N</i>-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-<i>d</i>]pyrimidine,...

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Bibliographic Details
Main Authors: Xiangyou Dong, Jie Tang, Chen Hu, Jiang Bai, Haixin Ding, Qiang Xiao
Format: Article
Language:English
Published: MDPI AG 2019-02-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/4/737
Description
Summary:In present paper, an expeditious total synthesis of naturally occurring 5&#8242;-deoxytoyocamycin and 5&#8242;-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at <i>N</i>-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-<i>d</i>]pyrimidine, a Vorbr&#252;ggen glycosylation with 1,2,3-tri-<i>O</i>-acetyl-5-deoxy-&#946;-D-ribofuranose afforded a completely regioselective <i>N</i>-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.
ISSN:1420-3049