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Single\u2010step access to a variety of 14\u2010 to 20\u2010membered macrolactones containing a tetrahydropyran ring was possible from readily available linear precursors in good yields and with moderate to excellent diastereoselectivity. A 13\u2010step synthesis of (\u2212)\u2010exiguolide, an anticancer marine macrolide, showcased the feasibility of our tandem reaction sequence for macrolactone synthesis and also demonstrated the power of transannular reactions for rapid assembly of the tetrahydropyran rings of the target natural product.<\/jats:p>","DOI":"10.1002\/anie.202202549","type":"journal-article","created":{"date-parts":[[2022,3,4]],"date-time":"2022-03-04T06:12:35Z","timestamp":1646374355000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Tandem Macrolactone Synthesis: Total Synthesis of (\u2212)\u2010Exiguolide by a Macrocyclization\/Transannular Pyran Cyclization Strategy"],"prefix":"10.1002","volume":"61","author":[{"given":"Daichi","family":"Mizukami","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry Faculty of Science and Engineering Chuo University  1-13-27 Kasuga, Bunkyo-ku Tokyo 112-8551 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see:"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00481F"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20200309"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.3390\/md14040065"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6NP00073H"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272819666150119225149"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3004778"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900634"},{"key":"e_1_2_7_19_1","unstructured":"For selected recent reviews see:"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00787B"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201505136"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC02913A"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201600803"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2262"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400215u"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527671304"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300271k"},{"key":"e_1_2_7_28_1","unstructured":"For selected examples in macrolactone synthesis 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exiguolide."},{"key":"e_1_2_7_99_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00382a053"},{"key":"e_1_2_7_100_1","unstructured":"Attempts at reversing the diastereoselectivity of the transannular Kishi reductive etherification by changing the Lewis acid (SnCl4) and\/or the solvent (toluene CH3CN Et2O tBuOMe) were uniformly unsuccessful."},{"key":"e_1_2_7_101_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo9708755"},{"key":"e_1_2_7_102_1","unstructured":"For 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