Iterative Polyketide Synthesis via a Consecutive Carbonyl-Protecting Strategy

Iterative Polyketide Synthesis via a Consecutive Carbonyl-Protecting Strategy
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DOI:
10.1021/acs.joc.8b00497
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发表时间:
2018-04-06
影响因子:
3.6
通讯作者:
Kudo, Kazuaki
Kudo, Kazuaki
中科院分区:
化学2区
文献类型:
--
作者:
Akagawa, Kengo;Kudo, Kazuaki

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为了解决保护β-聚羰基化合物的困难,展示了用于顺序保护延长羰基的方法。通过使用O-保护的肟官能团逐步形成异恶唑环,进行羧酸与丙二酸半硫酯的重复链延长,然后保护所得的β-酮硫酯。根据该程序合成了Yangonin和异樱花素。
To address the difficulty in protecting a beta-polycarbonyl compound, a method for the sequential protection of elongating carbonyl groups was demonstrated. The iterative chain elongation of a carboxylic acid with malonic acid half thioester followed by the protection of the resulting beta-ketothioester was performed via the stepwise formation of an isoxazole ring using an O-protected oxime functionality. Yangonin and isosakuranetin were synthesized according to this procedure.