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The key features of the synthesis include the highly convergent stereocontrolled construction of the monomeric hydroxy salicylate starting from asymmetric epoxidation of the \u03c3\u2010symmetrical dialkenyl carbinol, and an unprecedented direct dimerization through NaHMDS\u2010promoted double transesterification.<\/jats:p>","DOI":"10.1002\/anie.201404408","type":"journal-article","created":{"date-parts":[[2014,6,24]],"date-time":"2014-06-24T21:31:41Z","timestamp":1403645501000},"page":"8459-8462","source":"Crossref","is-referenced-by-count":26,"title":["Total Synthesis of Marinomycin\u2005A Based on a Direct Dimerization Strategy"],"prefix":"10.1002","volume":"53","author":[{"given":"Tatsuya","family":"Nishimaru","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masashi","family":"Kondo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kimito","family":"Takeshita","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keisuke","family":"Takahashi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Ishihara","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Susumi","family":"Hatakeyama","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,6,24]]},"reference":[{"key":"e_1_2_2_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0558948"},{"key":"e_1_2_2_2_2","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601867"},{"key":"e_1_2_2_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601867"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja068053p"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1330"},{"key":"e_1_2_2_6_2","unstructured":"\u00a0"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070240k"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo900945x"},{"key":"e_1_2_2_9_2","unstructured":"For selected recent examples of transesterification of salicylic acid acetonides see:"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802852r"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1258244"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo200332d"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo200337v"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol201863b"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103081"},{"key":"e_1_2_2_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103081"},{"key":"e_1_2_2_16_2","unstructured":"Nicolaou et\u2005al.[2]reported that the attempted double Suzuki dimerization to form the 44\u2010membered macrodiolide favored intramolecular cyclization to provide the 22\u2010membered macrolide. In addition Evans et\u2005al.[3]reported that the monomeric hydroxy salicylate with MOM protecting groups and an ethylidene acetal underwent base\u2010mediated decomposition."},{"key":"e_1_2_2_17_2","unstructured":"Molecular mechanical calculations (MMFF* Macro Model 8.6) suggested that the intramolecular cyclization of4to the 22\u2010membered macrolide was unlikely because of the remote distance between the salicic ester carbonyl and hydroxy group (7.562\u2005\u00c5). On the other hand the formation of 44\u2010membered macrodiolide28from the corresponding hydroxy salicylate generated by the initial transesterification looked favorable owing to the proximity of the reaction sites (3.489\u2005\u00c5). See the Supporting Information."},{"key":"e_1_2_2_18_2","unstructured":"For reviews:"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00039a007"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.5059\/yukigoseikyokaishi.63.312"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)81416-1"},{"key":"e_1_2_2_22_2","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1995-5141"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.77.1581"},{"key":"e_1_2_2_25_2","unstructured":"\u00a0"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)60143-0"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)01042-3"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01130-7"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-99-S60"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000817s"},{"key":"e_1_2_2_31_2","unstructured":"\u00a0"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850001759"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198601122"},{"key":"e_1_2_2_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19860980115"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00239a036"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.15227\/orgsyn.062.0009"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00345-6"},{"key":"e_1_2_2_37_2","unstructured":"\u00a0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397918908050700"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-5474"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-44346"},{"key":"e_1_2_2_41_2","unstructured":"\u00a0"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39810000465"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00145a004"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0528580"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(91)80675-V"},{"key":"e_1_2_2_46_2","first-page":"1306","author":"Higashibayashi S.","year":"2000","journal-title":"Synlett"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201404408","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201404408","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T15:44:10Z","timestamp":1697471050000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201404408"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,6,24]]},"references-count":49,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2014,8,4]]}},"alternative-id":["10.1002\/anie.201404408"],"URL":"https:\/\/doi.org\/10.1002\/anie.201404408","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,6,24]]}}}