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A highly stereoselective Horner\u2013Wadsworth\u2013Emmons (HWE) condensation of a C<jats:sub>17<\/jats:sub>\u2010allylphosphonate and a C<jats:sub>20<\/jats:sub>\u2010aldehyde was used as the last conjunctive step. Both a Sonogashira reaction to form the C<jats:sub>17<\/jats:sub>\u2010phosphonate and the final HWE condensation proved to be compatible with the sensitive C7\u2013C10 enyne <jats:italic>E<\/jats:italic> configuration. Regioselective (5\u2010<jats:italic>exo<\/jats:italic>\u2010dig) silver\u2010promoted lactonization reactions of three alternative pent\u20102\u2010en\u20104\u2010ynoic acid precursors with increased complexity, including a fully functionalized C<jats:sub>20<\/jats:sub>\u2010fragment, were explored for the preparation of the \u03b3\u2010alkylidenebutenolide fragment. This survey extends the existing methodologies for the preparation of oxygen\u2010containing carotenoids (xanthophylls) and streamlines the synthesis of additional members of the C<jats:sub>37<\/jats:sub>\u2010norcarotenoid butenolide family of natural products.<\/jats:p>","DOI":"10.1002\/chem.201301873","type":"journal-article","created":{"date-parts":[[2013,8,12]],"date-time":"2013-08-12T08:59:41Z","timestamp":1376297981000},"page":"13065-13074","source":"Crossref","is-referenced-by-count":22,"title":["Total Synthesis of Enantiopure Pyrrhoxanthin: Alternative Methods for the Stereoselective Preparation of 4\u2010Alkylidenebutenolides"],"prefix":"10.1002","volume":"19","author":[{"given":"Bel\u00e9n","family":"Vaz","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leticia","family":"Otero","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rosana","family":"\u00c1lvarez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u00c1ngel R.","family":"de\u2005Lera","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,8,12]]},"reference":[{"key":"e_1_2_5_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbabio.2011.04.012"},{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbabio.2012.02.002"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(74)85038-7"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02530961"},{"key":"e_1_2_5_5_2","volume-title":"Carotenoids. 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