791635-42-2Relevant academic research and scientific papers
Total synthesis of (-)-fasicularin and (-)-lepadiformine a based on zn-mediated allylation of chiral N-tert-butanesulfinyl ketimine
Mei, San-Lin,Zhao, Gang
experimental part, p. 1660 - 1668 (2010/06/21)
The stereoselective total synthesis of fasicularin (1) and lepadiformine A (2) is described, which features the utilization of a Zn-mediated allylation of a chiral, aliphatic, N-tertbutariesulfinyl ketimlne to construct the amino-substituted quaternary carbon center in good yield and with excellent diastereoselectivity. The azaspirocyclic scaffold was installed sequentially by a Sharpless dihydroxylation and an internal epoxide-opening reaction, and this scaffold was further converted into common intermediate S. Removing the tosyl (Ts) protecting group of 5 and reductively animating using Luche's reagent completed the synthesis of (-)-fasicularin (1), while reducing S using L-selectride, deprotecting the Ts group, and finishing with an intramolecular amino alcohol cyclocondensation completed the total synthesis of (-)lepadiformine A (2).
Total syntheses of (+)-cylindricines C-E and (-)-lepadiformine through a common intermediate derived from an aza-Prins cyclization and Wharton's rearrangement
Liu, Jia,Hsung, Richard P.,Peters, Scott D.
, p. 3989 - 3992 (2007/10/03)
(Chemical Equation Presented) Enantioselective total syntheses of (+)-cylindricines C-E and (-)-lepadiformine through a common tricyclic intermediate are described here. These syntheses are concise and feature an aza-Prins cyclization and a seldom-used Wh
