start-ver=1.4 cd-journal=joma no-vol=23 cd-vols= no-issue=68 article-no= start-page=17191 end-page=17194 dt-received= dt-revised= dt-accepted= dt-pub-year=2017 dt-pub=20171206 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Total Synthesis of Two Possible Diastereomers of Natural 6-Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation en-subtitle= kn-subtitle= en-abstract= kn-abstract= The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1 H and 13 C?NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1. en-copyright= kn-copyright= en-aut-name=TakamuraHiroyoshi en-aut-sei=Takamura en-aut-mei=Hiroyoshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=KatsubeTomoya en-aut-sei=Katsube en-aut-mei=Tomoya kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=OkamotoKazuki en-aut-sei=Okamoto en-aut-mei=Kazuki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=KadotaIsao en-aut-sei=Kadota en-aut-mei=Isao kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=2 en-affil= Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=3 en-affil= Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= affil-num=4 en-affil= Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University kn-affil= en-keyword=natural products kn-keyword=natural products en-keyword=stereoselective synthesis kn-keyword=stereoselective synthesis en-keyword=structure elucidation kn-keyword=structure elucidation en-keyword=tetrahydrofuran kn-keyword=tetrahydrofuran en-keyword=total synthesis kn-keyword=total synthesis END