{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T22:05:16Z","timestamp":1790460316084,"version":"4.1.0"},"reference-count":45,"publisher":"Wiley","issue":"40","license":[{"start":{"date-parts":[[2020,8,11]],"date-time":"2020-08-11T00:00:00Z","timestamp":1597104000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003006","name":"Eidgen\u00f6ssische Technische Hochschule Z\u00fcrich","doi-asserted-by":"publisher","award":["Institutional funding"],"award-info":[{"award-number":["Institutional funding"]}],"id":[{"id":"10.13039\/501100003006","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2020,9,28]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The total synthesis of the potent new antibiotic disciformycin\u2005B (<jats:bold>2<\/jats:bold>) is described, which shows significant activity against methicillin\u2010 and vancomycin\u2010resistant <jats:italic>Staphylococcus aureus<\/jats:italic> (MRSA\/VRSA) strains. The synthetic route is based on macrocyclization of a tetraene substrate to the 12\u2010membered macrolactone core by ring\u2010closing olefin metathesis (RCM). Although macrocyclization was accompanied by concomitant cyclopentene formation by an alternative RCM pathway, conditions were established to give the macrocycle as the major product. Key steps in the construction of the RCM substrate include a highly efficient Evans <jats:italic>syn<\/jats:italic>\u2010aldol reaction, the asymmetric Brown allylation of angelic aldehyde, and the stereoselective Zn(BH<jats:sub>4<\/jats:sub>)<jats:sub>2<\/jats:sub>\u2010mediated 1,2\u2010reduction of an enone. The synthesis was completed by late\u2010stage dehydrative glycosylation to introduce the <jats:sc>d<\/jats:sc>\u2010arabinofuranosyl moiety and final chemoselective allylic alcohol oxidation.<\/jats:p>","DOI":"10.1002\/anie.202004589","type":"journal-article","created":{"date-parts":[[2020,6,19]],"date-time":"2020-06-19T05:37:01Z","timestamp":1592545021000},"page":"17393-17397","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["An RCM\u2010Based Total Synthesis of the Antibiotic Disciformycin\u2005B"],"prefix":"10.1002","volume":"59","author":[{"given":"Philipp","family":"Waser","sequence":"first","affiliation":[{"name":"ETH Z\u00fcrich Department of Chemistry and Applied Biosciences Institute of Pharmaceutical Sciences  HCl H405, Vladimir-Prolog-Weg 4 CH-8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0747-9734","authenticated-orcid":false,"given":"Karl\u2010Heinz","family":"Altmann","sequence":"additional","affiliation":[{"name":"ETH Z\u00fcrich Department of Chemistry and Applied Biosciences Institute of Pharmaceutical Sciences  HCl H405, Vladimir-Prolog-Weg 4 CH-8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,8,11]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406973"},{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201406973"},{"key":"e_1_2_2_2_1","unstructured":"The molecular target of1and2has been suggested to be the bacterial RNA polymerase: J. Herrmann O. Kalinina F. Surup R. M\u00fcller Antibacterial disciformycins from myxobacteria as novel RNA polymerase inhibitors Presented at the 2ndEuropean Conference on Natural Products Frankfurt\/Main Germany September 6\u20139 2015."},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404291"},{"key":"e_1_2_2_4_1","doi-asserted-by":"crossref","unstructured":"US Department of Health Center for Disease Control (CDC). Antibiotic Resistance Threats in the United States 2019. DOI:https:\/\/doi.org\/10.15620\/cdc:82532.","DOI":"10.15620\/cdc:82532"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705550"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201701639"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1611559"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00665"},{"key":"e_1_2_2_9_1","unstructured":"For RCM-based macrocyclizations in competition with the formation of small rings see e.g.:"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol991214s"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/np030540k"},{"key":"e_1_2_2_12_1","unstructured":"For examples see:"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/np049728"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2835"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270071213"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.02.055"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00033a010"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197805221"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19780900718"},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0710360"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.09.010"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01508a026"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00170a070"},{"key":"e_1_2_2_24_1","unstructured":"\u00a0"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.27-0888"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01294a058"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97963-3"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00354a003"},{"key":"e_1_2_2_29_1","unstructured":"Neither the intermediate alcohol nor aldehyde10could be extensively purified due to their high volatility. In particular 10could only be isolated as a mixture with CH2Cl2. Thus an accurate yield for the allylation reaction could not be calculated. However the allylation was clean and gave9in estimated yields of around 80\u2009% from10(calculated based on the CH2Cl2content of10)."},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1981-29317"},{"key":"e_1_2_2_31_1","unstructured":"For examples see"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070571s"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990947"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035435u"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja710485n"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NP00048K"},{"key":"e_1_2_2_37_1","unstructured":"Separation was possible after the glycosylation step. See the SI for details."},{"key":"e_1_2_2_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja971067y"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00153a002"},{"key":"e_1_2_2_40_1","unstructured":"For the investigation of other conditions see the SI."},{"key":"e_1_2_2_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo981322c"},{"key":"e_1_2_2_42_1","unstructured":"NMR-spectroscopic data for2were in full agreement with those reported in the literature.[1 \u20095]The specific rotation of synthetic2was lower than reported for the natural material[1](i. e. [\u03b1]=+35 (c=0.2 MeOH) for synthetic2vs. [\u03b1]D=+64 (c=0.4 MeOH) for natural2). F\u00fcrstner and co-workers have reported [\u03b1]=+188 (c=0.04 MeOH).[5]Synthetic2co-eluted with natural2from a chiral normal phase Daicel Chiralpak AD-H column."},{"key":"e_1_2_2_43_1","unstructured":"As pointed out by one of the reviewers the difference in the efficiency of the RCM between dienes7and16may well be ascribed to differences in the degree of conformational pre-organization for ring-closure. This proposal is in line with observations by Ichikawa et\u2005al. in their studies towards the synthesis of gulmirecin A [8]where they observed a pronounced dependence of the efficiency (or even feasibility) of the Ni0-mediated reductive cyclization to the 12-membered ring on the structure of the ynal precursor."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.202004589","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202004589","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202004589","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202004589","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T02:52:17Z","timestamp":1693191137000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202004589"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,8,11]]},"references-count":45,"journal-issue":{"issue":"40","published-print":{"date-parts":[[2020,9,28]]}},"alternative-id":["10.1002\/anie.202004589"],"URL":"https:\/\/doi.org\/10.1002\/anie.202004589","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,8,11]]},"assertion":[{"value":"2020-03-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-08-11","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}