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- W2022995893 endingPage "4759" @default.
- W2022995893 startingPage "4745" @default.
- W2022995893 abstract "A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron rich and sterically hindered aromatic iodide and (2) a Lewis base-catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria." @default.
- W2022995893 created "2016-06-24" @default.
- W2022995893 creator A5060673018 @default.
- W2022995893 creator A5086108389 @default.
- W2022995893 creator A5005212587 @default.
- W2022995893 date "2010-06-01" @default.
- W2022995893 modified "2023-09-27" @default.
- W2022995893 title "Total synthesis of (+)-papulacandin D" @default.
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