Synthesis of the C19–C30 bis-THF fragment of iriomoteolide-13a via stepwise SN2 cyclization and intramolecular syn-oxypalladation
文献信息
发布日期
2021-10-05
DOI
10.1039/D1QO01049B
影响因子
5.281
作者
Hui Zhao, Haichen Ma, Tsz Chun Yip, Wei-Min Dai
查看原文
摘要
The C19–C30 bis-THF fragment of the proposed structure of iriomoteolide-13a has been synthesized. The ω-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by an anti-aldol reaction and asymmetric dihydroxylation (AD) as the key steps. Upon heating in pyridine, the stereotetrad underwent an SN2 cyclization to form the C19–C22 THF ring chemoselectively. The propargylic alcohol, after cleavage of the C28-OPMB ether, was reduced to the corresponding allylic alcohol with spontaneous removal of the C23-OTBS protecting group. Finally, the ene triol was subjected to the Pd(II)-catalyzed intramolecular syn-oxypalladation to give the C23–C26 THF ring with a dr value of 86 : 14. It was found that the C21-OH group, which might form a chelated Pd(II) complex along with the C23-OH group, was tolerated during the syn-oxypalladation process.
相关文献
Highly branched triple-chain surfactant-mediated electrochemical exfoliation of graphite to obtain graphene oxide: colloidal behaviour and application in water treatment
Nur Amirah Jamaluddin, Suriani Abu Bakar, Tretya Ardyani, Masanobu Sagisaka, Shota Suhara, Mohamad Hafiz Mamat, Mohd Khairul Ahmad, Stephen M. King, Sarah E. Rogers, Julian Eastoe
2020-05-19
Paper
DOI: 10.1039/D0CP01243B
Intramolecular vibrational energy redistribution and the quantum ergodicity transition: a phase space perspective
Sourav Karmakar, Srihari Keshavamurthy
2020-04-20
Perspective
DOI: 10.1039/D0CP01413C
Density-functional theory models of Fe(iv)O reactivity in metal–organic frameworks: self-interaction error, spin delocalisation and the role of hybrid exchange
Fernan Saiz, Leonardo Bernasconi
2020-05-26
Paper
DOI: 10.1039/D0CP01285H
Elastic and electronic origins of strain stabilized photovoltaic γ-CsPbI3
Zhigang Li, Yan Qin, Liyuan Dong, Kai Li, Yang Qiao, Wei Li
2020-05-22
Paper
DOI: 10.1039/D0CP01649G
Quantum kinetic energy and isotope fractionation in aqueous ionic solutions
Lu Wang, Michele Ceriotti, Thomas E. Markland
2020-01-08
Paper
DOI: 10.1039/C9CP06483D
Introducing mesoscopic charge transfer rates into molecular electronics
Adriano Santos, Ushula M. Tefashe, Richard L. McCreery, Paulo R. Bueno
2020-04-27
Communication
DOI: 10.1039/D0CP01621G
UV-visible absorption spectrum of FAD and its reduced forms embedded in a cryptochrome protein
Karno Schwinn, Nicolas Ferré, Miquel Huix-Rotllant
2020-05-07
Paper
DOI: 10.1039/D0CP01714K
Formation of hydroperoxo (–OOH) species on the surface of self-doped Bi2.15WO6: reactivity towards As(iii) oxidation
Xiang-Ming Wang, Song-Hai Wu, Hai-Tao Ren, Peng-Yue Zhu, Cong Wang, Yong Liu, Shi-Wei Sun, Xiao-Cong Zhang, Yi-Ying Lin, Zi-He Meng, Shao-Yi Jia
2020-05-12
Paper
DOI: 10.1039/D0CP00569J
Quantifying anisotropic dielectric response properties of nanoconfined water within graphene slit pores
Sergi Ruiz-Barragan, Saskia Körning, Dominik Marx
2020-04-27
Communication
DOI: 10.1039/D0CP00916D
您可能还喜欢
化合物问答
如何储存1,2-环己二酮环乙缩醛(CAS号：4746-96-7)？
1,2-环己二酮环乙缩醛应储存在阴凉、干燥、通风良好的地方，避免阳光直射。建议使用密封容器保存，并保持环境温度在室温范围内，远离火源和热源。
4746-96-71,4-Dioxaspiro[4.5]d...
化合物问答
Ecopladib(CAS号：381683-92-7)的市场或研究趋势如何？
Ecopladib作为一种新型的药物，主要应用于治疗高胆固醇等疾病。目前，市场和研究趋势显示，Ecopladib因其独特的药理作用而受到关注。随着对心血管疾病治...
381683-92-7Ecopladib
化合物问答
2,3-Dimethyl-3H-imidazo[4,5-c]pyridine(CAS号：52538-09-7)通常如何合成？
2,3-二甲基-3H-咪唑[4,5-c]吡啶通常通过咪唑和2,3-二甲基吡啶的缩合反应合成。具体来说，将咪唑和2,3-二甲基吡啶在适当的溶剂中进行加热或加压反应...
52538-09-72,3-Dimethyl-3H-imid...
化合物问答
2,3,4,5-tetrahydro-1H-3-苯并氮杂环;盐酸盐(CAS号：17379-01-0)的市场或研究趋势如何？
该化合物在药物化学和有机合成中有一定的应用。近年来，随着对新型药物化合物的需求增加，该化合物的研究趋势主要集中在探索其生物活性，尤其是其在神经系统疾病治疗中的潜...
17379-01-02,3,4,5-Tetrahydro-1...
68-90-6(2-Ethyl-1-benzofura...
化合物问答
如何储存盐酸甘氨酸丁酯(CAS号：13048-99-2)？
盐酸甘氨酸丁酯应储存在阴凉、干燥、通风良好的地方，避免阳光直射和高温环境，温度应控制在25℃以下。储存容器应密封，避免与空气中的水分和酸性物质接触，以防发生水解...
13048-99-2Butyl glycinate hydr...
化合物问答
什么是2-Iodo-N,N-dimethylbenzamide(CAS号：54616-46-5)？
2-碘-N,N-二甲基苯胺是一种有机化合物，化学名为2-Iodo-N,N-dimethylbenzamide。其分子式为C<sub>9</sub>H<sub>1...
54616-46-52-Iodo-N,N-dimethylb...
16817-90-6N-Cyclohexylglycinam...
化合物问答
5-溴-2-(4H-1,2,4-三唑-4-基)吡啶(CAS号：959240-99-4)的市场或研究趋势如何？
随着医药、农药和新材料领域的发展，该化合物作为关键中间体的应用日益增多。特别是在药物合成中，由于其独特的化学性质，可以用于合成多种药物分子。未来的研究趋势可能集...
959240-99-45-Bromo-2-(4H-1,2,4-...
化合物问答
2,4-二溴-6-三氟甲基嘧啶(CAS号：785778-00-9)通常如何合成？
2,4-二溴-6-三氟甲基嘧啶通常通过溴化反应合成。首先，将6-三氟甲基嘧啶与溴化剂（如液溴）在适当的溶剂（如二氯甲烷、四氢呋喃）中反应，加入适当的催化剂（如四...
785778-00-92,4-Dibromo-6-(trifl...
来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
推荐化合物
![1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile structure](https://cnstatic.chemtradehub.com/structs/143/1434747-57-5-fc0d.webp "1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile structure")
2,2-dideuterio-2-(3,4,5,6-tetradeuterio-2-pyridyl)acetic acid;hydrochloride
CAS号:
1329799-67-8
分子式:
C7H2ClD6NO2
推荐供应商
免责声明
本页面提供的学术期刊信息仅供参考和研究使用。我们与任何期刊出版商均无关联，也不处理投稿事宜。如有投稿相关咨询，请直接联系相关期刊出版商。
如发现页面信息有误，请发送邮件至 support@chemtradehub.com 联系我们。我们将及时核实并处理您的问题。