{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T20:34:49Z","timestamp":1790627689663,"version":"4.1.0"},"reference-count":101,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2014,11,6]],"date-time":"2014-11-06T00:00:00Z","timestamp":1415232000000},"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":[[2015,1,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Molybdenum\u2010, tungsten\u2010, and ruthenium\u2010based complexes that control the stereochemical outcome of olefin metathesis reactions have been recently introduced. However, the complementary nature of these systems through their combined use in multistep complex molecule synthesis has not been illustrated. A concise diastereo\u2010 and enantioselective route that furnishes the anti\u2010proliferative natural product neopeltolide is now disclosed. Catalytic transformations are employed to address every stereochemical issue. Among the featured processes are an enantioselective ring\u2010opening\/cross\u2010metathesis promoted by a Mo monoaryloxide pyrrolide (MAP) complex and a macrocyclic ring\u2010closing metathesis that affords a trisubstituted alkene and is catalyzed by a Mo bis(aryloxide) species. Furthermore, <jats:italic>Z<\/jats:italic>\u2010selective cross\u2010metathesis reactions, facilitated by Mo and Ru complexes, have been employed in the stereoselective synthesis of the acyclic dienyl moiety of the target molecule.<\/jats:p>","DOI":"10.1002\/anie.201409120","type":"journal-article","created":{"date-parts":[[2014,11,6]],"date-time":"2014-11-06T17:45:42Z","timestamp":1415295942000},"page":"215-220","source":"Crossref","is-referenced-by-count":67,"title":["Catalyst\u2010Controlled Stereoselective Olefin Metathesis as a Principal Strategy in Multistep Synthesis Design: A Concise Route to (+)\u2010Neopeltolide"],"prefix":"10.1002","volume":"54","author":[{"given":"Miao","family":"Yu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard R.","family":"Schrock","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Amir H.","family":"Hoveyda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,11,6]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"For reviews regarding the use of catalytic OM reactions in natural product synthesis see:"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500369"},{"key":"e_1_2_2_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500369"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527629626.ch10"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo500467z"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527629626.ch5"},{"key":"e_1_2_2_6_2","unstructured":"ForZ\u2010selective ROCM reactions promoted by Mo alkylidenes see:"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja900097n"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja210946z"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja304827a"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4046422"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja404208a"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309430"},{"key":"e_1_2_2_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309430"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310767"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201310767"},{"key":"e_1_2_2_14_2","unstructured":"ForZ\u2010selective CM reactions with Mo or W alkylidene complexes see:"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature09957"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja403188t"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302538"},{"key":"e_1_2_2_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302538"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206079"},{"key":"e_1_2_2_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206079"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3SC52806E"},{"key":"e_1_2_2_20_2","unstructured":"ForZ\u2010selective MRCM reactions with Mo or W complexes see:"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10563"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204045"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209180"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209180"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311916m"},{"key":"e_1_2_2_25_2","unstructured":"For previous enantioselective approaches to the total synthesis of neopeltolide see:"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704122"},{"key":"e_1_2_2_26_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704122"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja710080q"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800386"},{"key":"e_1_2_2_28_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800386"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801399"},{"key":"e_1_2_2_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801399"},{"key":"e_1_2_2_30_2","first-page":"4704","author":"Paterson I.","year":"2008","journal-title":"Chem. 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see the Supporting Information for details."},{"key":"e_1_2_2_60_2","unstructured":"The minor diastereoisomer from enantioselective boronate conjugate addition (95:5 e.r.) was removed by column chromatography on silica gel of ester9."},{"key":"e_1_2_2_61_2","unstructured":"\u00a0"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00149a048"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00166a023"},{"key":"e_1_2_2_64_2","unstructured":"\u00a0"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature07594"},{"key":"e_1_2_2_66_2","unstructured":"see Ref.\u2005[9]."},{"key":"e_1_2_2_67_2","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990909q"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001179g"},{"key":"e_1_2_2_70_2","unstructured":"For reviews on Suzuki\u2010type catalytic cross\u2010coupling reactions see:"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600089"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700984"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/om400584f"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00111a025"},{"key":"e_1_2_2_75_2","unstructured":"\u00a0"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008000"},{"key":"e_1_2_2_76_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201008000"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01171-7"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.01.139"},{"key":"e_1_2_2_79_2","unstructured":"For total synthesis initiatives where catalytic transformations are the principal strategic elements see:"},{"key":"e_1_2_2_80_2","unstructured":"Ref.\u2005[10];"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700501"},{"key":"e_1_2_2_81_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700501"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10232"},{"key":"e_1_2_2_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400605"},{"key":"e_1_2_2_83_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201400605"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature13735"},{"key":"e_1_2_2_85_2","unstructured":"A.\u2005W.\u2005H. 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