1. Synthetic Studies on Presporolide, a Putative Enediyne Precursor of Sporolides
- Author
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Eri Ozeki, Yujiro Hayashi, Masahiro Hirama, Shuji Yamashita, and Kanae Terayama
- Subjects
Bicyclic molecule ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Alcohol ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Reagent ,Enediyne ,Moiety ,Stereoselectivity ,Physical and Theoretical Chemistry - Abstract
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.
- Published
- 2017