image

Total synthesis of Tedanolide, 13-Deoxy- (Part 2):
Reference: Smith, A. B.; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. J. Am. Chem. Soc 2003, 125, 350. DOI (Part 1) (Part 3)
Keywords: Alkyl-OH → Aldehyde • Ketal → Diol-1,2 • O-SiEt3 → O-H • O-SEM → O-H • O-SiiPr3 → O-H • Yamaguchi lactonization • Lactone-9+ • O-H → O-SiEt3 • O-PMB → O-H • Ketal(thio) → Ketone • Alkyl-OH → Ketone • Epoxidation, peracid • CompOx-Alkene/Alkene+Peracid • Evans-Tishchenko reduction • Li/H → Li-Dithiane • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R •
Reagents: DMSO, Py·SO3 (Parikh-Doering) • SmI2 • TsOH·Py • Hydroxide, lithium • Benzoyl chloride, 2,4,6-trichloro • HF·Py • MgBr2 • Perbenzoic acid, 3-chloro • Fluoride, R4N+ • DMAP • SiEt3-Cl • DDQ • Iodosobenzene-TFA • Dess-Martin • BuLi(tert), HMPA •

Syntheses Home