{"title":"Total Syntheses of Marine Natural Products Lyngbyabellin O and Lyngbyabellin P.","authors":"Jing Chen, Shiyu Li, Chao Xu, Tao Ye","doi":"10.3390/md23090340","DOIUrl":null,"url":null,"abstract":"<p><p>Lyngbyabellins O and P are complex natural products derived from non-ribosomal peptide synthetase/polyketide synthase (NRPS/PKS) biosynthetic pathways and have been isolated from marine cyanobacterial sources. Both metabolites are characterized by the presence of two thiazole rings and a distinctive dichlorinated <i>β</i>-hydroxy acid side chain. Notably, lyngbyabellin P is further distinguished by the incorporation of a (3<i>R</i>,4<i>S</i>)-statine moiety. Herein, we report the first total syntheses of lyngbyabellins O and P, which are achieved through the convergent coupling of three key synthetic fragments, namely, two enantiomerically enriched thiazole subunits and a hydroxycarboxylic acid derivative, the latter constructed via a stereoselective aldol reaction. The total syntheses were completed in 12 and 13 longest linear steps (LLSs) for lyngbyabellins O and P, respectively, furnishing the natural products in overall yields of 5.6% and 2.5%.</p>","PeriodicalId":18222,"journal":{"name":"Marine Drugs","volume":"23 9","pages":""},"PeriodicalIF":5.4000,"publicationDate":"2025-08-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12471755/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Marine Drugs","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.3390/md23090340","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
Lyngbyabellins O and P are complex natural products derived from non-ribosomal peptide synthetase/polyketide synthase (NRPS/PKS) biosynthetic pathways and have been isolated from marine cyanobacterial sources. Both metabolites are characterized by the presence of two thiazole rings and a distinctive dichlorinated β-hydroxy acid side chain. Notably, lyngbyabellin P is further distinguished by the incorporation of a (3R,4S)-statine moiety. Herein, we report the first total syntheses of lyngbyabellins O and P, which are achieved through the convergent coupling of three key synthetic fragments, namely, two enantiomerically enriched thiazole subunits and a hydroxycarboxylic acid derivative, the latter constructed via a stereoselective aldol reaction. The total syntheses were completed in 12 and 13 longest linear steps (LLSs) for lyngbyabellins O and P, respectively, furnishing the natural products in overall yields of 5.6% and 2.5%.
期刊介绍：
Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.
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