Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides.
Shuji YamashitaKanae TerayamaEri OzekiYujiro HayashiMasahiro HiramaPublished in: Organic letters (2017)
A synthesis of the core framework of presporolide, which possesses both a strained bicyclo[7.3.0]dodecadiyne moiety and a distinctive macrolactone structure, is reported. This synthesis features: (i) a Cu-mediated O-arylation of a hindered tertiary alcohol using triarylbismuth reagent; (ii) stereoselective construction of the strained nine-membered diyne ring; and (iii) atroposelective formation of the macrolactone.
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