{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T16:44:18Z","timestamp":1791218658003,"version":"4.1.0"},"reference-count":225,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2014,12,17]],"date-time":"2014-12-17T00:00:00Z","timestamp":1418774400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"MPG"},{"name":"Alexander-von-Humboldt Foundation"},{"name":"JSPS"},{"name":"Fonds der Chemischen Industrie"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2015,2,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The marine natural products amphidinolide\u2005C (<jats:bold>1<\/jats:bold>) and F (<jats:bold>4<\/jats:bold>) differ in their side chains but share a common macrolide core with a signature 1,4\u2010diketone substructure. This particular motif inspired a synthesis plan predicating a late\u2010stage formation of this non\u2010consonant (\u201cumpoled\u201d) pattern by a platinum\u2010catalyzed transannular hydroalkoxylation of a cycloalkyne precursor. This key intermediate was assembled from three building blocks (<jats:bold>29<\/jats:bold>, <jats:bold>41<\/jats:bold> and <jats:bold>47<\/jats:bold> (or <jats:bold>65<\/jats:bold>)) by Yamaguchi esterification, Stille cross\u2010coupling and a macrocyclization by ring\u2010closing alkyne metathesis (RCAM). This approach illustrates the exquisite alkynophilicity of the catalysts chosen for the RCAM and alkyne hydroalkoxylation steps, which activate triple bonds with remarkable ease but left up to five other \u03c0\u2010systems in the respective substrates intact. Interestingly, the inverse chemoselectivity pattern was exploited for the preparation of the tetrahydrofuran building blocks <jats:bold>47<\/jats:bold> and <jats:bold>65<\/jats:bold> carrying the different side chains of the two target macrolides. These fragments derive from a common aldehyde precursor <jats:bold>46<\/jats:bold> formed by an exquisitely alkene\u2010selective cobalt\u2010catalyzed oxidative cyclization of the diunsaturated alcohol <jats:bold>44<\/jats:bold>, which left an adjacent acetylene group untouched. The northern sector <jats:bold>29<\/jats:bold> was prepared by a two\u2010directional Marshall propargylation strategy, whereas the highly adorned acid subunit <jats:bold>41<\/jats:bold> derives from <jats:sc>D<\/jats:sc>\u2010glutamic acid by an intramolecular oxa\u2010Michael addition and a proline\u2010mediated hydroxyacetone aldol reaction as the key steps; the necessary Me<jats:sub>3<\/jats:sub>Sn\u2010group on the terminus of <jats:bold>41<\/jats:bold> for use in the Stille coupling was installed via enol triflate <jats:bold>39<\/jats:bold>, which was obtained by selective deprotonation\/triflation of the ketone site of the precursor <jats:bold>38<\/jats:bold> without competing enolization of the ester also present in this particular substrate.<\/jats:p>","DOI":"10.1002\/chem.201405790","type":"journal-article","created":{"date-parts":[[2014,12,17]],"date-time":"2014-12-17T10:41:53Z","timestamp":1418812913000},"page":"2398-2408","source":"Crossref","is-referenced-by-count":86,"title":["Concise Total Syntheses of Amphidinolides\u2005C and F"],"prefix":"10.1002","volume":"21","author":[{"given":"Ga\u00eblle","family":"Valot","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Damien","family":"Mailhol","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher S.","family":"Regens","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel P.","family":"O'Malley","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Edouard","family":"Godineau","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroshi","family":"Takikawa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petra","family":"Philipps","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alois","family":"F\u00fcrstner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,12,17]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/np0605844"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b310427n"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00210a029"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol015741z"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)00142-X"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.3390\/md203083"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-10-S(E)3"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.44.1259"},{"key":"e_1_2_6_11_2","volume-title":"Macrolide Antibiotics. 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