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(<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010steroselectivity is the most critical issue in their synthesis, however, (<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010 stereocomplementary synthetic methods remain quite limited. The present account discloses general (<jats:italic>E<\/jats:italic>)\u2010, (<jats:italic>Z<\/jats:italic>)\u2010stereocomplementary syntheses of a variety of \u03b1,\u03b2\u2010unsaturated esters from highly accessible (<jats:italic>E<\/jats:italic>)\u2010, (<jats:italic>Z<\/jats:italic>)\u2010stereodefined enol tosylates derived from \u03b2\u2010ketoesters and \u03b1\u2010formyl esters. Step 1 toward the stereocomplementary preparation of (<jats:italic>E<\/jats:italic>)\u2010, (<jats:italic>Z<\/jats:italic>)\u2010stereodefined enol tosylates is implemented by using inexpensive reagents under mild reaction conditions. Step 2 toward the highly stereoretentive synthesis of (<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010stereodefined \u03b1,\u03b2\u2010unsaturated esters involves Suzuki\u2010Miyaura, Negishi, Sonogashira, Iron\u2010catalyzed, Mizoroki\u2010Heck, and Buchwald\u2010Hartwig cross\u2010coupling reactions. Notably, this strategy was successfully applied for parallel drug syntheses of (<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010zimelidine, (<jats:italic>E<\/jats:italic>)\u2010 and (<jats:italic>Z<\/jats:italic>)\u2010tamoxifen, and Merck's cyclopropane pharmacophore. Representative successful utilizations by other groups are also introduced.<\/jats:p>","DOI":"10.1002\/tcr.202000076","type":"journal-article","created":{"date-parts":[[2020,9,16]],"date-time":"2020-09-16T07:24:03Z","timestamp":1600241043000},"page":"1410-1429","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Stereocomplementary and Parallel Syntheses of Multi\u2010Substituted (<i>E<\/i>)\u2010, (<i>Z<\/i>)\u2010Stereodefined \u03b1,\u03b2\u2010Unsaturated Esters: Application to Drug Syntheses"],"prefix":"10.1002","volume":"20","author":[{"given":"Yuichiro","family":"Ashida","sequence":"first","affiliation":[{"name":"Department of Chemistry, School of Science and Technology Kwansei Gakuin University  2-1 Gakuen Sanda Hyogo 669-1337 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3265-4343","authenticated-orcid":false,"given":"Yoo","family":"Tanabe","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Science and Technology Kwansei Gakuin University  2-1 Gakuen Sanda Hyogo 669-1337 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,9,15]]},"reference":[{"key":"e_1_2_14_1_1","first-page":"792","volume-title":"Advanced Organic Chemistry, 6 th","author":"Smith M. 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