Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration.,Journal of Natural Products

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Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-19 , DOI: 10.1021/acs.jnatprod.9b00570
Dariya A Romanova ₁ , David L Avetyan _{1,

2} , Maxim L Belyanin ₁ , Elena V Stepanova _{1,

3}

Affiliation

In the present work, the synthesis of acetylated salicins, which occur naturally in many Salicaceae species, is reported. The preparation of 2-O-acetylsalicin, 2-O-acetylchlorosalicin, and 2-O-acetylethylsalicin from peracetylated bromosalicin with selective acid-catalyzed deacetylation and one-pot nucleophilic substitution of bromine as the key steps is described. The base-catalyzed O-2 → O-6 acetyl migration afforded 6-O-acetylsalicin derivatives in good yields. Thus, the first synthesis of 6-O-acetylsalicin (fragilin) using acetyl group migration is reported as well as the synthesis of 6-O-acetylchlorosalicin and 6-O-acetylethylsalicin. The NaOMe-catalyzed deacetylation of acetylated glycosides gave salicin, chlorosalicin, and ethylsalicin recently reported from Alangium chinense.

中文翻译：

利用选择性脱乙酰基和乙酰基团迁移合成杨柳科乙酰水杨素。

在目前的工作中，已报道了许多水杨科物种中天然存在的乙酰化水杨素的合成。描述了由过乙酰化的溴水杨素以选择性酸催化的脱乙酰基作用和一锅式亲核取代溴为关键步骤制备2-O-乙酰水杨素，2-O-乙酰氯水杨素和2-O-乙酰乙基水杨素的方法。碱催化的O-2→O-6乙酰基迁移得到了6-O-乙酰水杨酸衍生物，收率很高。因此，报道了使用乙酰基迁移的第一个6-O-乙酰水杨素（fragilin）合成以及6-O-乙酰氯水杨素和6-O-乙酰乙基水杨素的合成。NaOMe催化的乙酰化糖苷的脱乙酰作用产生了最近从Alangium chinense报道的水杨素，氯水杨素和乙基水杨素。

更新日期：2020-03-19

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