image

Total synthesis of FR-900848:
Keywords: O-SiPh2tBu → O-H • Alkyl-OH → CarboxAcid • O-SiPh2tBu → O-H • O-SiPh2tBu → O-H • HWE → DienoateEster • Barton decarboxylation • C-CO2H → C-Br • Li/Sn → Li-Cyclopropyl • Cu-Alkyl Oxidation • Peterson → EneSulfide • O-H → O-SiPh2tBu • Simmons-Smith • Cyclopropane • Cu-Alkyl Oxidation • Alkyl-OH → Aldehyde • Li/H → Li-Sulfone • EneSulfone → Vinyl-H • CarboxAcid → CarboxEster(thio) • CarboxAcid → CarboxAmide • CarboxAcid → CarboxEster(thio) • Alkyl-OH → Aldehyde • CarboxEster → CarboxAcid •
Reagents: Fluoride, R4N+ • Periodate, sodium • Mercaptopyridine-N-oxide • Carbodiimide • DMAP • BrCCl3 • BuLi(tert) • O2 • Fluoride, R4N+ • RuO4-Pr4N+, NMO • BuLi(n) • EneSulfone • Li°Naphth • Fluoride, R4N+ • RuO4-Pr4N+, NMO • P(O)(OR)2CH2-Vinyl • LiN(SiMe3)2 • Hydroxide, lithium • Carbodiimide • DMF (solvent) • Vinyl-SnR3 • CH2I2, ZnEt2 • Imidazole • BuLi(sec) • O2 • Chiral catalyst •

Syntheses Home