717919-08-9Relevant academic research and scientific papers
Stereoselective ketal-tethered intramolecular Diels-Alder cycloadditions. An approach to the 2-oxadecalin spiroketal core of antifungal agent fusidilactone C
Wang, Jiashi,Hsung, Richard P.,Ghosh, Sunil K.
, p. 1939 - 1942 (2004)
Equation presented. An approach toward the 2-oxadecalin spiroketal core of fusidilactone C via a rare ketal-tethered intramolecular Diels-Alder cycloaddition is described here. This intramolecular Diels-Alder cycloaddition is highly endo-selective and ove
A cyclic acetal tethered intramolecular diels-alder cycloaddition. studies directed toward a total synthesis of (±)-fusidilactone C
Ghosh, Sunil K.,Wei, Yonggang,Gerasyuto, Aleksey I.,Feltenberger, John B.,Wang, Jiashi,Hsung, Richard P.
experimental part, p. 1379 - 1409 (2011/05/14)
Efforts toward a synthesis of (±)-fusidilactone C is described here featuring a novel cyclic acetal tethered intramolecular Diels-Alder strategy. This unique and facile IMDA turned out to be highly endo-selective [endo-I and endo-II], as assessed from our mechanistic analyses. When using protic solvents or Lewis acids, the endo-I selectivity was greatly enhanced. Thus, it proved to be a real challenge to circumvent this excellent stereochemical outcome, which is undesired for the total synthesis, as an exo-II selectivity is desired. Progress was made to use the endo-II cycloadduct and to access the desired trans-2-oxadecalin motif in (±)-fusidilactone C. The Japan Institute of Heterocyclic Chemistry.
