121194-85-2Relevant articles and documents
ASYMMETRIC TOTAL SYNTHESES OF (-)-TYLOPHORINE VIA THE HIGHLY ENANTIOSELECTIVE INTRAMOLECULAR DOUBLE MICHAEL REACTION
Ihara, Masataka,Takino, Yoshinobu,Fukumoto, Keiichiro,Kametani, Tetsuji
, p. 4135 - 4138 (1988)
Asymmetric total synthesis of (-)-tylophorine (2) was achieved with a high enantioselectivity through the intramolecular double Michael reaction of the α , β -unsaturated ester (8) having a novel chiral auxiliary with tert.-butyldimethylsilyl trifluoromethanesulfonate and Et3N.
Asymmetric Total Synthesis of Naturally Occurring (R)-(-)-Enantiomer of Tylophorine via Intramolecular Double Michael Reaction
Ihara, Masataka,Takino, Yoshinobu,Tomotake, Mayumi,Fukumoto, Keiichiro
, p. 2287 - 2292 (2007/10/02)
The first asymmetric total synthesis of the naturally occurring (R)-(-)-enantiomer (1) of tylophorine was achieved with high enantioselectivity via the intramolecular double Michael reaction of α,β-unsaturated esters (10) and (20), having two different chiral auxiliaries, with t-butyldimethylsilyl trifluoromethanesulphonate in the presence of triethylamine. (-)-Phenylmenthol and (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-5-hydroxy-2-phenyl-1,3-dioxane, readily available from D-glucose, were used as chiral auxiliaries.