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This result is remarkable in view of the failed attempts documented in the literature at converting electron deficient alkynes with the aid of more classical catalysts. The subsequent <jats:italic>Z<\/jats:italic>\u2010selective semi\u2010reduction of the resulting cycloalkyne by hydrogenation over nickel boride required careful optimization in order to minimize overreduction and competing dehalogenation of the compound's alkenyl iodide terminus as needed for final attachment of the side chain of <jats:bold>1<\/jats:bold> by Sonogashira coupling. The required cyclization precursor itself was prepared via Kocienski olefination.<\/jats:p>","DOI":"10.1002\/chem.201804988","type":"journal-article","created":{"date-parts":[[2018,11,6]],"date-time":"2018-11-06T04:09:18Z","timestamp":1541477358000},"page":"255-259","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Total Synthesis of Callyspongiolide, Part 2: The Ynoate Metathesis\/<i>cis<\/i>\u2010Reduction Strategy"],"prefix":"10.1002","volume":"25","author":[{"given":"Bernhard","family":"W\u00f6lfl","sequence":"first","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Guillaume","family":"Mata","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0098-3417","authenticated-orcid":false,"given":"Alois","family":"F\u00fcrstner","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,12,11]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403241v"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03533"},{"key":"e_1_2_7_3_1","unstructured":"\u00a0"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01523"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB02051H"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13591"},{"key":"e_1_2_7_7_1","unstructured":"For studies towards callyspongiolide see:"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB01007E"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02897"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.08.041"},{"key":"e_1_2_7_11_1","unstructured":"For our most recent contributions see ref.\u2005[23a] and the following:"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201808937"},{"key":"e_1_2_7_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201808937"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05094"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510026"},{"key":"e_1_2_7_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201510026"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804987"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204513"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204513"},{"key":"e_1_2_7_17_1","unstructured":"For recent applications of RCAM to natural product synthesis reported by other groups see the following for leading references:"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501922"},{"key":"e_1_2_7_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501922"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201512005"},{"key":"e_1_2_7_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201512005"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2016.02.050"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03137"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01312"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300576"},{"key":"e_1_2_7_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300576"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0528580"},{"key":"e_1_2_7_25_1","unstructured":"\u00a0"},{"key":"e_1_2_7_26_2","author":"F\u00fcrstner A.","journal-title":"J. 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