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These alkaloids have a unique chemical structure characterized by the <jats:italic>trans<\/jats:italic>\u20101\u2010azadecalin (AB ring system) fused with the spirocyclic ring (AC ring system). Here we found that a cycloisomerization reaction from functionalized linear substrates to a 1\u2010azaspiro[4.5]decane framework corresponding to the AC ring in lepadiformines is promoted by a catalytic amount of mercury(II) triflate (Hg(OTf)<jats:sub>2<\/jats:sub>). The total syntheses of (\u2212)\u2010lepadiformines\u2005A and B were achieved in 28\u2009% and 21\u2009% overall yields, respectively, through the novel cycloisomerization reaction. The syntheses of (+)\u2010 and (\u2212)\u2010lepadiformine\u2005C hydrochloride salts also enabled us to determine the absolute configuration of natural lepadiformine\u2005C. It has been found that a phenomenon of enantiodivergence occurs in lepadiformine alkaloids from a single species of marine tunicate, <jats:italic>Clavelina moluccensis<\/jats:italic>. The cytotoxic activities of synthesized lepadiformine hydrochloride salts and their synthetic intermediates were evaluated.<\/jats:p>","DOI":"10.1002\/chem.201701475","type":"journal-article","created":{"date-parts":[[2017,5,10]],"date-time":"2017-05-10T07:58:55Z","timestamp":1494403135000},"page":"9535-9545","source":"Crossref","is-referenced-by-count":22,"title":["Total Syntheses of Lepadiformine Marine Alkaloids with Enantiodivergency, Utilizing Hg(OTf)<sub>2<\/sub>\u2010Catalyzed Cycloisomerization Reaction and their Cytotoxic Activities"],"prefix":"10.1002","volume":"23","author":[{"given":"Keisuke","family":"Nishikawa","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Osaka City University  Sumiyoshi-ku Osaka 558\u20138585 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kengo","family":"Yamauchi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Osaka City 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