54541-88-7Relevant articles and documents
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.