214117-56-3Relevant academic research and scientific papers
Total synthesis of (2R,4S,2′S,3′R)-hydroxyitraconazole: Implementations of a recycle protocol and a mild and safe phase-transfer reagent for preparation of the key chiral units
Tanoury, Gerald J.,Hett, Robert,Wilkinson, H. Scott,Wald, Stephen A.,Senanayake, Chris H.
, p. 3487 - 3493 (2003)
A convergent total synthesis of enantiomerically-pure (2R,4S,2′S, 3′R)-hydroxyitraconazole 1b is described. The left dioxolane portion of the molecule was prepared in good yield by the conversion of (S)-10 to the corresponding enantiomerically and diastereomerically-pure acetonide (2R,4R)-3 by a recycle protocol involving diastereoselective crystallization of the tosylate salt, followed by re-equilibration of the mother liquor and crystallization. The right-hand triazolone moeity (2S,3R)-4 was generated by alkyaltion of triazolone 6 with enantiomerically pure cyclic sulfate (4R,5R)-7 under mild and essentially non-hazardous reaction conditions (TDA-1, K 2CO3, acetonitrile).
Pd-catalyzed aminations of aryl triazolones: Effective synthesis of hydroxyitraconazole enantiomers
Tanoury, Gerald J.,Senanayake, Chris H.,Hett, Robert,Kuhn, Amy M.,Kessler, Donald W.,Wald, Stephen A.
, p. 6845 - 6848 (2007/10/03)
A palladium-catalyzed amination of triazolone 3 by piperazine 2 was used as the key step in an efficient synthesis of highly enantiomerically-pure hydroxyitraconazole isomers. Compound 2 (>99%ee) was prepared by reaction of an achiral phenol precursor wit
