Sequential Dieckmann cyclization enables the total synthesis of 7-epi-clusianone and 18-hydroxy-7-epi-clusianone

文献情報

出版日 2023-12-13

DOI 10.1039/D3OB01840G

インパクトファクター 3.876

著者

Yunhui Wan, Huaimo Wu, Linhao Xia, Song Liu, Yi Ren, Hongxi Xu, Changwu Zheng

原文を見る

要旨

A unified approach for the construction of the bicyclo[3.3.1]nonane-2,4,9-trione core of polycyclic polyprenylated acylphloroglucinols (PPAPs) was reported. This approach involves a sequential process of two distinct Dieckmann condensation reactions from the linear precursor. Using this method, the divergent total synthesis of the natural products 7-epi-clusianone and 18-hydroxy-7-epi-clusianone and the formal synthesis of sampsonione P were achieved. Additionally, other key steps to realize this strategy include RuCl3-catalyzed oxidative olefin cleavage and Pd-catalyzed Tsuji–Trost decarboxylative allylation. The synthesis indicated that bicyclo[3.3.1]nonane-2,4,9-triones could also be constructed via 6-membered intermediates.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Sequential Dieckmann cyclization enables the total synthesis of 7-epi-clusianone and 18-hydroxy-7-epi-clusianone

文献情報

おすすめジャーナル

関連文献

When amine-based conducting polymers meet Au nanoparticles: suppressing H2 evolution and promoting the selective electroreduction of CO2 to CO at low overpotentials

The controlled synthesis of V-doped MoS2-NixSy hollow nanospheres and their electrocatalytic performance in hydrogen evolution reaction

A facile preparation of PEO–LiClO4–fumed SiO2 composite solid-state electrolyte with improved electrochemical performance for lithium-metal batteries

A facile method of selective dissolution for preparation of Co3O4/LaCoO3 as a bifunctional catalyst for Al/Zn–air batteries

A solution processed Sb2S3-based photocathode with enhanced photocatalytic performance via constructing an ultrathin TiO2 overlayer and noble metal modification

Correction: High performance binder-free Fe–Ni hydroxides on nickel foam prepared in piranha solution for the oxygen evolution reaction

Towards practical cells: combined use of titanium black as a cathode additive and sparingly solvating electrolyte for high-energy-density lithium–sulfur batteries

Fine-tuning the water oxidation performance of hierarchical Co3O4 nanostructures prepared from different cobalt precursors

Morphologically controlled rapid fabrication of rhodium sulfide (Rh2S3) thin films for superior and robust hydrogen evolution reaction

Techno-economic analysis of a sustainable process for converting CO2 and H2O to feedstock for fuels and chemicals

こちらもおすすめ

5-苄基四氢吡咯并[3,4-c]吡咯-1,3[2H,3ah]-二酮の主な用途は何ですか？

唾液酸路易ス Aを取り扱う際の実験室安全事項は何ですか？

タルトブチル ((1-(2-クロロアセチル)ピペリジン-4-イルメチル)カーバamatはどの業界で使用されていますか？

3-烯丙基-2-羟基苯甲醛の物理化学的性質は何ですか？

乳清酸 Potassium Orotateとは何ですか？

4-甲基苯磺酸异丙酯はどの業界で使用されていますか？

6-(3- Florobenzen)-N-[1-(2,2,2- Trifluoroethyl)-4-Piperidinyl]-3-Pyridinycarboxamideはどの業界で使用されていますか？

左西孟旦はどのように合成されますか？

3-乙氧基哌啶盐酸盐に適用される法規ガイドラインは何ですか？

Diethyl (hydroxymethyl)phosphonateの主な用途は何ですか？

掲載誌

Organic & Biomolecular Chemistry

おすすめ化合物

[3-Formyl-5-(trifluoromethoxy)phenyl]boronic acid

Ethyl 5-[({[(2-methyl-2-propanyl)oxy]carbonyl}amino)methyl]-1,2-oxazole-3-carboxylate

5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Ethyl 2,2-dimethyl-3-phenylpropanoate

3-(3-Carboxyphenyl)-5-(trifluoromethyl)benzoic acid

おすすめサプライヤー