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HFIP-Promoted Short Total Synthesis of Gochnatiolide D and Ainsliadimer A from Dehydrozaluzanin C
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-18 , DOI: 10.1002/ejoc.202400533
Antonis Kelesidis 1 , Kyriaki Gennaiou 1 , Alexandros L. Zografos 2
Affiliation  

The total syntheses of gochnatiolide D and ainsliadimer A were achieved through a streamlined one-pot sequence starting from their biogenetic precursor dehydrozaluzanin C. These biomimetic, protecting group-free syntheses involve the elegant orchestration of the highly diastereoselective hetero-Diels-Alder reaction of dehydrozaluzanin C, its subsequent hydrolysis to gochnatiolide D and finally an aldol reaction to ainsliadimer A, all harnessed by the hydrogen bond propensity and acidity of hexafluoroisopropanol (HFIP), which was utilized as the reaction solvent.

中文翻译:


HFIP 促进从脱氢扎鲁扎宁 C 短时间全合成 Gochnatiolide D 和 Ainsliadimer A



gochnatiolide D 和 ainsliadimer A 的全合成是通过从它们的生物前体 dehydrozaluzanin C 开始的简化的一锅法序列实现的。这些仿生、无保护基团的合成涉及脱氢zaluzanin 的高度非对映选择性杂 Diels-Alder 反应的优雅编排C,随后水解为 gochnatiolide D,最后通过羟醛反应生成 ainsliadimer A,所有这些都是通过六氟异丙醇 (HFIP) 的氢键倾向和酸性来利用的,六氟异丙醇 (HFIP) 用作反应溶剂。
更新日期:2024-06-18
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