1357255-88-9Relevant articles and documents
Reversing the reactivity of carbonyl functions with phosphonium salts: Enantioselective total synthesis of (+)-centrolobine
Fujioka, Hiromichi,Yahata, Kenzo,Kubo, Ozora,Sawama, Yoshinari,Hamada, Tomohito,Maegawa, Tomohiro
supporting information; experimental part, p. 12232 - 12235 (2012/01/30)
Step saver: Carbonyl groups with lower reactivities can be transformed in the presence of more reactive ones by treatment with PPh3 (or PEt3) and TMSOTf prior to the reaction (see scheme; TMS=trimethylsilyl, Tf=trifluoromethanesulfonyl). This methodology can be applied to reduction and alkylation reactions, and enabled the short asymmetric total synthesis of (+)-centrolobine with the highest overall yield reported to date.