Total synthesis of Cystothiazole A, C:
| Reference: | Williams, D. R.; Patnaik, S.; Clark, M. P. J. Org. Chem. 2001, 66, 8463. DOI |
| Reactions: | CarboxEster enolate+Aldehyde • Thiazole synthesis • Mechanism • HWE → EnoateEster • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • EnoateEster → Allyl-OH • Allyl-OH → Enal • CarboxAmide(Evans) → CarboxEster • O-H → O-Me • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Alkyl-OH → KetoEster • Ketone → EnolEther • CarboxEster → Aldehyde • |
| Reagents: | AlHiBu2 • NaH • AlHiBu2 • Me-MgBr • MeI • Dess-Martin • AlHiBu2 • CH2=C(OLi)(OR) • LiNiPr2 • Dess-Martin • Sulfate, dimethyl • SiiPr3-OTf • Bromopyruvate • DMSO, (COCl)2 (Swern) • DMSO (solvent) • NaH • Chiral auxiliary (amide-Evans) • Chiral auxiliary (amide-Evans) • P(O)(OR)2CH2-C(O)OR' • HOMe (react) • HMPA (solvent) • Fluoride, R4N+ • |