{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T07:46:52Z","timestamp":1791100012435,"version":"4.1.0"},"reference-count":85,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2009,4,17]],"date-time":"2009-04-17T00:00:00Z","timestamp":1239926400000},"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":[[2009,5,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>Weaving an intricate web<\/jats:bold>: A stereoselective synthesis of (\u2212)\u2010agelastatin\u2005A has been developed, which requires 11\u2005steps from commercially available starting material. The application of a Rh\u2010catalyzed intramolecular olefin aziridination reaction and the subsequent manipulation of the resulting tricyclic intermediate (see scheme) punctuate this study.<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p>","DOI":"10.1002\/anie.200806292","type":"journal-article","created":{"date-parts":[[2009,4,19]],"date-time":"2009-04-19T15:11:22Z","timestamp":1240153882000},"page":"3802-3805","source":"Crossref","is-referenced-by-count":103,"title":["A Stereoselective Synthesis of the Bromopyrrole Natural Product (\u2212)\u2010Agelastatin\u2005A"],"prefix":"10.1002","volume":"48","author":[{"given":"Paul\u2005M.","family":"Wehn","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J.","family":"Du\u2005Bois","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,5,4]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For reviews on bromopyrrole natural products see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1015748018820"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527205774370531"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/b700206h"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701798"},{"key":"e_1_2_2_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701798"},{"key":"e_1_2_2_6_2","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39930001305"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19940770720"},{"key":"e_1_2_2_9_2","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/np9703813"},{"key":"e_1_2_2_11_2","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19960790315"},{"key":"e_1_2_2_13_2","doi-asserted-by":"crossref","first-page":"11","DOI":"10.3727\/096504005775082075","volume":"15","author":"Pettit G. R.","year":"2005","journal-title":"Oncol. Res."},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1158\/1535-7163.MCT-07-2251"},{"key":"e_1_2_2_15_2","unstructured":"It has also been suggested that agelastatin\u2005A inhibits GSK\u20103\u03b2 an enzyme implicated in the development of the neurofibrillary tangles associated with Alzheimer\u2019s disease see:"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(00)00063-6"},{"key":"e_1_2_2_17_2","unstructured":"For completed syntheses see:"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja992487l"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja027121e"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026287v"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035036l"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0490476"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol047634l"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja061105q"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0709735"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802225g"},{"key":"e_1_2_2_27_2","unstructured":"For an approach to agelastatin\u2005A involving intermolecular aziridination see:"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)02238-9"},{"key":"e_1_2_2_29_2","unstructured":"\u00a0"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035776u"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol051896l"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.07.099"},{"key":"e_1_2_2_33_2","unstructured":"For additional examples of intramolecular aziridination in natural products synthesis see:"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00203a055"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981310r"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9823893"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0500129"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200400657"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200400657"},{"key":"e_1_2_2_39_2","unstructured":"P.\u2005M. Wehn Ph.D. Thesis Stanford University (USA) 2006."},{"key":"e_1_2_2_40_2","unstructured":"For examples of rhodium\u2010catalyzed intramolecular aziridination using sulfonamide and carbamate substrates see:"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0270475"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01409-6"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2004.01.015"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048990k"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0500129"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0510973"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701288"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0358877"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0552850"},{"key":"e_1_2_2_50_2","unstructured":"For selected examples of copper\u2010catalyzed intramolecular azirdination with sulfonamide and sulfamate substrates see:"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol000130c"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010968a"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0200899"},{"key":"e_1_2_2_54_2","first-page":"1251","author":"Esteoule A.","year":"2007","journal-title":"Synthesis"},{"key":"e_1_2_2_55_2","unstructured":"\u00a0"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(99)00146-7"},{"key":"e_1_2_2_57_2","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01130-8"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011033x"},{"key":"e_1_2_2_60_2","unstructured":"\u00a0"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0446294"},{"key":"e_1_2_2_62_2","unstructured":"We refer to this heterocycle as an oxathiazepane for convenience."},{"key":"e_1_2_2_63_2","unstructured":"Ring opening of related bicyclic aziridines generally favors the oxathiazepane ring. For a complete discussion on this subject see reference\u2005[8\u2009c]."},{"key":"e_1_2_2_64_2","unstructured":"\u00a0"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00284-9"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol7022104"},{"key":"e_1_2_2_67_2","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01507a045"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050622q"},{"key":"e_1_2_2_70_2","unstructured":"Tricarbonyl13was prepared in two steps: 1)\u2005addition of H2C\uf8feCHCH2CH2MgBr to dibenzyl oxalate; 2)\u2005O3 CH2Cl2 \u221278\u2009\u00b0C; then Ph3P and was used immediately following chromatographic purification."},{"key":"e_1_2_2_71_2","unstructured":"For a general review on pyrrole synthesis see:"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1080\/00304940109356613"},{"key":"e_1_2_2_73_2","first-page":"918","author":"Tracey M. 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