54541-88-7Relevant academic research and scientific papers
Unconventional Fragment Usage Enables a Concise Total Synthesis of (-)-Callyspongiolide
Manoni, Francesco,Rumo, Corentin,Li, Liubo,Harran, Patrick G.
supporting information, p. 1280 - 1284 (2018/02/09)
An asymmetric synthesis of (-)-callyspongiolide is described. The route builds the macrolide domain atypically from a disaccharide and a monoterpene without passing through a seco-acid. Chiral iridium catalysis selectively joins fragments. Subsequent degradation of an imbedded butyrolactone via perhemiketal fragmentation affords a stereo- and regio-defined homoallylic alcohol that is engaged directly in a carbonylative macrolactonization. Further elaboration of the polyunsaturated appendage provides the natural product in a particularly direct and flexible manner.
Expeditious total syntheses of natural allenic products via aromatic ring umpolung
Sabot, Cyrille,Berard, Didier,Canesi, Sylvain
supporting information; experimental part, p. 4629 - 4632 (2009/05/27)
(Chemical Equation Presented) Concise diastereoselective syntheses of the marine (±)-panacene and terrestrial (±)-desbromopanacene have been achieved in a few steps based on a concept of aromatic ring umpolung . The synthetic avenue to the (±)-panacene involved a novel oxymercuration strategy to produce the correct configuration of the bromoallene moiety.
