| 19 | 0 | 46 |
| 下载次数 | 被引频次 | 阅读次数 |
本研究报道了具有抗螨虫活性的天然产物AB3217A及其衍生物的模块化合成。以易得的茴香霉素和D-木糖硫苷衍生物为起始原料,通过木糖C2位苯甲酸酯的邻基参与效应调控的立体选择性木糖β-糖苷键的形成和DDQ(2,3-二氯-5,6-二氰基-1,4-苯醌)介导的分子内交叉脱氢醚化反应作为关键步骤,经9—10步反应以5.6%~8.9%的总收率实现了AB3217A及其结构类似物的合成,从而为其生物活性研究奠定了物质基础。
Abstract:A modular synthesisof AB3217A with antimite activity and its analogues has been achieved. The synthesis uses the readily accessible anisomycin and D-thioxylofuranoside derivative as the starting materials, and involves stereoselective β-xylofuranosidic bond construction directed by the neighboring group participation of the C2-benzoate in the xylofuranosyl residue, and a DDQ-promoted intramolecular cross-dehydrogenative etherification reaction as the key transformations. Through this integrated approach, AB3217A and its structural analogues were successfully synthesized in 9 to 10 steps sequence with overall yields of 5.6%~8.9%, thereby establishing a foundation of material basis for biological evaluation in future.
[1] Kanbe K,Mimura Y,Tamamura T,et al.AB3217-A,a novel anti-mite substance produced by a strain of Streptomyces platensis[J].The Journal of Antibiotics,1992,45:458-464.
[2] Kanbe K,Takahashi A,Tamamura T,et al.Isolation and structures of two novel anti-mite substances,AB3217-B and C[J].The Journal of Antibiotics,1992,45:568-571.
[3] Choi H,Engene N,Byrum T,et al.Dragocins A-D,structurally intriguing cytotoxic metabolites from a Panamanian Marine Cyanobacterium[J].Organic Letters,2018,21:266-270.
[4] Nakata M,Tamai T,Kamio T,et al.The Total synthesis of AB3217-A,a novel anti-mite substance,via intermolecular etherification and intramolecular glycosylation[J].Bulletin of the Chemical Society of Japan,1994,67:3057-3066.
[5] Smith B P,Truax N J,Pollatos A S,et al.Total synthesis of dragocins A-C through electrochemical cyclization[J].Angewandte Chemie International Edition,2024,136:e202401107.
[6] Wang Z,Wang J,Wang P,et al.Modular synthesis and cytotoxicity evaluation of dragocins A-C and their analogues:Discovery of a potential anticancer agent[J].Chinese Journal of Chemistry,2025,43:1107-1113.
[7] Xu Y,Zhang Q,Xiao Y,et al.Practical synthesis of latent disarmed S-2-(2-propylthio) benzyl glycosides for interrupted Pummerer reaction mediated glycosylation[J].Tetrahedron Letters,2017,58:2381-2384.
[8] Joe M,Sun D,Taha H,et al.The 5-deoxy-5-methylthio-xylofuranose residue in mycobacterial lipoarabinomannan.Absolute stereochemistry,linkage position,conformation,and immunomodulatory activity[J].Journal of the American Chemical Society,2006,128:5059-5072.
[9] Fontana C,Widmalm G.Primary structure of glycans by NMR spectroscopy[J].Chemical Reviews,2023,123:1040-1102.
[10] van Rijssel E R,van Delft P,Lodder G,et al.Furanosyl oxocarbenium ion stability and stereoselectivity[J].Angewandte Chemie International Edition,2014,53:10381-10385.
[11] Kumar V,Sharma A,Sharma M,et al.DDQ catalyzed benzylic acetoxylation of arylalkanes:A case of exquisitely controlled oxidation under sonochemical activation[J].Tetrahedron,2007,63:9718-9723.
[12] Hartrampf N,Winter N,Pupo G,et al.Total synthesis of the norhasubanan alkaloid stephadiamine[J].Journal of the American Chemical Society,2018,140:8675-8680.
[13] Li C J.Cross-dehydrogenative coupling (CDC):Exploring C-C bond formations beyond functional group transformations[J].Accounts of Chemical Research,2009,42:335-344.
[14] Krylov I B,Vil V A,Terent’ev A O.Cross-dehydrogenative coupling for the intermolecular C-O bond formation[J].BeilsteinJournal of Organic Chemistry,2015,11:92-146.
[15] Grigorenko N A,Khomutov A R,Keinänen T A,et al.Synthesis of novel optical isomers of α-methylpolyamines[J].Tetrahedron,2007,63:2257-2262.
[16] Khomutov M,Mikhura I,Kochetkov S N,et al.C-methylated analogs of spermine and spermidine:Synthesis and biological activity[J].Russian Journal of Bioorganic Chemistry,2019,45:463-487.
基本信息:
DOI:10.16441/j.cnki.hdxb.20250135
中图分类号:O629
引用信息:
[1]孙超民,王自强,王鹏,等.AB3217A及其衍生物的模块化合成[J].中国海洋大学学报(自然科学版),2026,56(05):113-119.DOI:10.16441/j.cnki.hdxb.20250135.
基金信息:
国家自然科学基金项目(22377114); 青岛海洋科技中心专项经费(2022QNLM030003-2)资助~~
2026-04-27
2026-04-27