Synthesis of functional allyl-α-tetrahydropyrones from cyrene

IF 1.8 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Mendeleev Communications Pub Date : 2024-07-01 DOI:10.1016/j.mencom.2024.06.016

引用次数: 0

Abstract

Addition of allylzinc to cyrene affords diastereomeric 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols. Opening of their 1,6-anhydro bridge with Ac₂O followed by selective deacetylation of the resulting tertiary and acetal acetates yields diastereomeric 2-acetoxymethyl-5-allyl-tetrahydro- pyran-5,6-diols whose oxidation by the action of DMSO–Ac₂O system is accompanied by etherification of tertiary hydroxy groups leading to methylthiomethoxy pyrone derivatives. The opening of 1,6-anhydro bridge in 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols with MeOH–HCl followed by oxidation with PCC gives individual (4S,6S)- 1-allyl-6-methoxy-2,5-dioxabicyclo[2.2.2]octan-3-one.

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从芘合成功能性烯丙基-α-四氢吡喃酮

将烯丙基锌加到芘中可得到非对映的 4-烯丙基-6,8-二氧双环[3.2.1]辛烷-4-醇。用 Ac2O 打开其 1,6-anhydro 桥，然后选择性地对生成的叔羟基和缩醛乙酸酯进行脱乙酰化反应，得到非对映的 2-乙酰氧甲基-5-烯丙基-四氢吡喃-5,6-二醇，在 DMSO-Ac2O 系统的作用下，这些二醇被氧化，同时叔羟基发生醚化反应，生成甲硫甲氧基吡喃酮衍生物。用 MeOH-HCl 打开 4-烯丙基-6,8-二氧杂环[3.2.1]辛烷-4-醇中的 1,6-脱水桥，然后用 PCC 氧化，可得到 (4S,6S)-1-烯丙基-6-甲氧基-2,5-二氧杂环[2.2.2]辛烷-3-酮。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Mendeleev Communications 化学-化学综合

CiteScore

3.00

自引率

21.10%

发文量

226

审稿时长

4-8 weeks

期刊介绍： Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications. Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.

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