image

Total synthesis of Cystothiazole A, C:
Reference: Williams, D. R.; Patnaik, S.; Clark, M. P. J. Org. Chem. 2001, 66, 8463. DOI
Keywords: CarboxEster → Aldehyde • EnoateEster → Allyl-OH • CarboxAmide(Evans) → CarboxEster • O-H → O-Me • Alkyl-OH → Aldehyde • CarboxEster → Alkyl-OH • Alkyl-OH → KetoEster • CarboxEster enolate+Aldehyde • Thiazole synthesis • Mechanism • HWE → EnoateEster • Allyl-OH → Enal • Ketone → EnolEther • Aldol-B-Evans •
Reagents: AlHiBu2 • P(O)(OR)2CH2-CO2R • NaH • AlHiBu2 • MeMgBr • MeI • Dess-Martin • AlHiBu2 • CH2=C(OLi)(OR) • LiNiPr2 • Dess-Martin • Sulfate, dimethyl • SiiPr3-OTf • Bromopyruvate • DMSO, (COCl)2 (Swern) • DMSO (solvent) • NaH • HMPA (solvent) • Chiral auxiliary-Evans •

Syntheses Home