{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T00:59:59Z","timestamp":1773881999591,"version":"3.50.1"},"reference-count":72,"publisher":"Wiley","issue":"33","license":[{"start":{"date-parts":[[2013,7,24]],"date-time":"2013-07-24T00:00:00Z","timestamp":1374624000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2013,8,12]]},"DOI":"10.1002\/anie.201304691","type":"journal-article","created":{"date-parts":[[2013,7,24]],"date-time":"2013-07-24T23:07:31Z","timestamp":1374707251000},"page":"8736-8741","source":"Crossref","is-referenced-by-count":32,"title":["Total Synthesis and Structural Revision of Viridicatumtoxin\u2005B"],"prefix":"10.1002","volume":"52","author":[{"given":"K. C.","family":"Nicolaou","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian","family":"Nilewski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher R. H.","family":"Hale","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Heraklidia A.","family":"Ioannidou","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Abdelatif","family":"ElMarrouni","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lizanne G.","family":"Koch","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,7,24]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200600350"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200600350"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801695"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801695"},{"key":"e_1_2_2_4_2","unstructured":"\u00a0"},{"key":"e_1_2_2_5_2","doi-asserted-by":"crossref","DOI":"10.1128\/9781555817886","volume-title":"Antibiotics, Actions, Origins, Resistance, 1st\u2005ed.","author":"Walsh C.","year":"2003"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867043455774"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nm1145"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/431899a"},{"key":"e_1_2_2_9_2","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00875a063"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01082a056"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)90501-X"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01004a041"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01025a063"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/j39710002215"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00497a035"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00274a072"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960434n"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2000.646"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302691j"},{"key":"e_1_2_2_21_2","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052151d"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1109755"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol071377d"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806629e"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.09.143"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1sc00303h"},{"key":"e_1_2_2_28_2","unstructured":"\u00a0"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/0041-008X(73)90057-4"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.2307\/3760103"},{"key":"e_1_2_2_31_2","unstructured":"\u00a0"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39760000728"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0567740882010759"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2008.84"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2012.83"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules18010204"},{"key":"e_1_2_2_37_2","unstructured":"\u00a0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39820000902"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39880001562"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/b911518h"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2010.03.015"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja206906d"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3028636"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)80182-3"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1080\/00304949809355262"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo034165c"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00479a060"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00215a003"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.03.095"},{"key":"e_1_2_2_50_2","unstructured":"Mechanistic studies of the one\u2010pot procedure involving the use of DBU on related systems suggested a stepwise pathway. The use of a strong base (i.e. NaH or LDA) with homophthalic anhydrides and quinones (Tamura Diels\u2013Alder reaction) is typically depicted as a concerted [4+2] cycloaddition but the synchronicity of the reaction has been questioned:"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352591"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352591"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr8002714"},{"key":"e_1_2_2_53_2","unstructured":"CCDC\u2005941202 941203 and 945867 contain the supplementary crystallographic data for compounds23 29 and38 respectively for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif. Compounds23and29were prepared by similar routes to those described herein and will be reported in the full account of this work."},{"key":"e_1_2_2_54_2","unstructured":"\u00a0"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00357a047"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8009732"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(81)89023-5"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00062a021"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.03.093"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973846k"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00231-1"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)00533-4"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071007k"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)72145-9"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00219a035"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.11.062"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00348a039"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_2_69_2","unstructured":"We thank Professor W.\u2010G. Kim for kindly providing us with the1H and13C\u2005NMR spectra of natural viridicatumtoxin\u2005B obtained at 300\u2005MHz and 226\u2005MHz respectively from a small sample of natural material. These spectroscopic data were in accord with those obtained by us at 600\u2005MHz and 151\u2005MHz for synthetic material thus confirming the identity of the two samples (except for the racemic nature of ours). Furthermore we noted certain discrepancies in the reported chemical shift values in Ref.\u2005[7] compared to those actually found in the provided spectra of the natural product. In particular the originally unreported carbonyl resonance near\u03b4=194\u2005ppm which we assigned as C5 was indeed present in the scanned authentic spectrum of the natural product. For the spectra of the natural and synthetic materials and further details see the Supporting Information."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201304691","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201304691","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T05:12:11Z","timestamp":1697433131000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201304691"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,7,24]]},"references-count":72,"journal-issue":{"issue":"33","published-print":{"date-parts":[[2013,8,12]]}},"alternative-id":["10.1002\/anie.201304691"],"URL":"https:\/\/doi.org\/10.1002\/anie.201304691","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,7,24]]}}}