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- W2317766073 abstract "A total synthesis of brevisamide, a marine monocyclic ether amide isolated from the dinoflagellate Karenia brevis, has been achieved in 18 steps starting from 4-(benzyloxy)butanol. The synthesis involves oxiranyl anion coupling between an epoxy sulfone and a triflate, intramolecular etherification of a hydroxy-bromoketone, diastereoselective introduction of the axial methyl group by hydroxyl-directed hydrogenation of an exocyclic olefin, and installation of an acetamide side chain by nucleophilic substitution of an N-acetyl carbamate. The dienal side chain is assembled using a Horner–Wadsworth–Emmons reaction to complete the synthesis." @default.
- W2317766073 created "2016-06-24" @default.
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- W2317766073 date "2016-04-22" @default.
- W2317766073 modified "2023-10-16" @default.
- W2317766073 title "Total Synthesis of Brevisamide Using an Oxiranyl Anion Strategy" @default.
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- W2317766073 doi "https://doi.org/10.1021/acs.joc.6b00484" @default.
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