Total synthesis of FR-900848:
| Reference: | Falck, J. R.; Mekonnen, B.; Yu, J.; Lai, J.-L. J. Am. Chem. Soc. 1996, 118, 6096 DOI |
| Reactions: | O-SiPh2tBu → O-H • O-SiPh2tBu → O-H • O-SiPh2tBu → O-H • HWE → DienoateEster • Barton decarboxylation • C-CO2H → C-Br • Li/Br → 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 • Alkyl-OH → CarboxAcid • Li-Sulfone+Aldehyde • Li-Silane+Aldehyde • |
| Reagents: | Fluoride, R4N+ • Periodate, sodium • Mercaptopyridine-N-oxide • Carbodiimide • DMAP • BrCCl3 • BuLi(tert) • O2 • Fluoride, R4N+ • RuO4-Pr4N+, NMO • LiCHR-Sulfonyl • BuLi(n) • EneSulfone • Li°/Naphth • Fluoride, R4N+ • RuO4-Pr4N+, NMO • P(O)(OR)2CH2-Vinyl • LiN(SiMe3)2 • Hydroxide, lithium • Carbodiimide • Thiol, aryl • DMF (solvent) • B(OR)2Alkyl • Vinyl-SnR3 • CH2I2, ZnEt2 • Imidazole • BuLi(sec) • O2 • Chiral catalyst (diol) • LiCHR-Sulfonyl • |