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Chem"},{"key":"10.1016\/j.bmcl.2021.128104_b0100","doi-asserted-by":"crossref","first-page":"3810","DOI":"10.1016\/j.ejmech.2009.04.005","volume":"44","author":"Santos","year":"2009","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmcl.2021.128104_b0105","unstructured":"Synthesis of podophyllotoxin-cytisine twin compounds (I\u2013IV): A solution of compounds 5\u20138 (0.17 mmol), 9a\u2013d (0.19 mmol), N,N'-diisopropylcarbodiimide (DIC, 0.24 mmol) and 4-dimethylaminopyridine (DMAP, 0.03 mmol) in dichloromethane (4 mL) was stirred at room temperature for 0.5\u201315 h. Then the mixture was diluted by ethyl acetate (30 mL), washed by 0.1 M aq. HCl (10 mL), 5% aq. NaHCO3 (10 mL) and brine (10 mL), dried over anhydrous Na2SO4, concentrated, and purified by preparative thin-layer chromatography (PTLC) to produce compounds I\u2013IV in 14%\u201360% yields. Data for Ia: (two rotamers, ratio: 56:44): Yield: 51%, white solid, m.p. 154-156 oC; [\u03b1]20D\u00a0=\u00a0\u221242 (c 2.2 mg\/mL, CHCl3); IR cm-1 (KBr): 2931, 1735, 1651, 1579, 1479, 1233, 1124, 996, 867, 799; 1H NMR (500 MHz, CDCl3) \u03b4: 7.27\u20137.30 (m, 1H, H-4''), 6.80 (s, 0.56H, H-5), 6.77 (s, 0.44H, H-5), 6.50 (s, 1H, H-8), 6.44\u20136.48 (m, 1H, H-3''), 6.37 (s, 2H, H-2', 6'), 6.05\u20136.08 (m, 1H, H-5''), 5.95\u20135.97 (m, 2H, OCH2O), 5.85 (d, J\u00a0=\u00a06.0 Hz, 0.56H, H-4), 5.83 (d, J\u00a0=\u00a06.0 Hz, 0.44H, H-4), 4.80 (d, J\u00a0=\u00a013.0 Hz, 0.44H), 4.66 (d, J\u00a0=\u00a013.0 Hz, 0.56H), 4.57 (d, J\u00a0=\u00a04.0 Hz, 1H, H-1), 4.33\u20134.36 (m, 0.45H), 4.14\u20134.22 (m, 1.58H), 3.99\u20134.09 (m, 2H), 3.88\u20133.93 (m, 1H), 3.81 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.44 (d, J\u00a0=\u00a012.5 Hz, 0.44H), 3.39 (d, J\u00a0=\u00a012.5 Hz, 0.56H), 3.10 (s, 0.44H, H-7''), 3.08 (s, 0.56H, H-7''), 2.77\u20132.92 (m, 3H), 2.65\u20132.72 (m, 1H), 2.45\u20132.62 (m, 4H), 2.03\u20132.10 (m, 2H, H-8''). HRMS (ESI): Calcd for C37H38N2O11Na ([M+Na]+), 709.2367; found, 709.2345."},{"key":"10.1016\/j.bmcl.2021.128104_b0110","doi-asserted-by":"crossref","first-page":"1410","DOI":"10.1016\/j.bmcl.2018.02.018","volume":"28","author":"Yang","year":"2018","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2021.128104_b0115","doi-asserted-by":"crossref","first-page":"4131","DOI":"10.1021\/acs.jafc.9b08242","volume":"68","author":"Hao","year":"2020","journal-title":"J Agric Food Chem"}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X21003309?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X21003309?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:41:35Z","timestamp":1760773295000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X21003309"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7]]},"references-count":23,"alternative-id":["S0960894X21003309"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2021.128104","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2021,7]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Insecticidal activity of twin compounds from podophyllotoxin and cytisine","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2021.128104","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2021 Elsevier Ltd. 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