Journal
SYNLETT
Volume 30, Issue 12, Pages 1401-1418Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611775
Keywords
artemisinin; cyclopamine; D-isocitric acid; hyperforin; epigenetics; sialic acid; transesterification; IBX
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Funding
- Human Frontier Science Program
- Deutsche Forschungsgemeinschaft
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In this Account we present the total syntheses of artemisinin (an important antimalarial agent) and cyclopamine (the first natural inhibitor of the hedgehog signaling pathway). Furthermore, we describe the design and development of a gamma-butyrolactone as an inhibitor of Gcn5 (a histone N-acetyltransferase), discuss the discovery of hyperforin and guttiferon G as the first natural products acting as inhibitors of sirtuins, and present the design of inhibitors of sialic acid biosynthesis. The biomedical background and importance are also discussed. Finally, we present the discovery and development of methods for transesterification, IBX-mediated oxidations, reduction of several functional groups with LiBH4/Me3SiCl, as well as a process enabling the synthesis of kilogram amounts of D-isocitric acid and its transformation to valuable chiral derivatives.
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