Total synthesis of Latrunculin B New:
| Reference: | Smith, III, A. B.; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995-3007 DOI |
| Reactions: | O-SiMe2tBu → O-H • N-H → N-PMB • CarboxEster → CarboxAcid • CarboxAcid → CarboxCl • CarboxCl+Mg-R • Mg-Alkyl+CarboxCl • Li-Alkynyl+Chlorocarbonate • Li/H → Li-Alkynyl • Carbocupration Alkyne • Cu-Alkyl+Alkyne • CarboxEster → CarboxAcid • Alkyl-X → Alkyl-I • Finkelstein reaction • Alkyl-X → Alkyl-PRn • Baeyer-Villiger • Lactone-6 • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • Lactone → Orthoester • Ozonolysis • Aldol-BR2 → Aldol • Orthoester → CarboxEster • Ketone → Ketal(Me) • O-H → O-SiMe2tBu • CarboxEster → Aldehyde • Wittig-alkyl → Ene-cis • Mitsunobu → Lactone-9+ • Alkyl-OH → Alkyl-OC(O)R • Lactone-9+ • Ketal → Ketone • N-PMB → N-H • |
| Reagents: | PMB-Br • NaH • Oxalyl chloride • Hydroxide, potassium • Me-MgBr • Perbenzoic acid, 3-chloro • Bicarbonate, sodium • LiNiPr2 • MeI • Chiral auxiliary (diol) • O3; PPh3 • Sulfonic acid, Camphor • B(OTf)Bu2 • NEtiPr2 • HCl, H2O • Sulfonic acid, Camphor • HOMe (react) • AlHiBu2 • BuLi(n) • O=C(OMe)Cl • Me-Cuprate • Hydroxide, lithium • Iodide, sodium • Acetone (solvent) • PPh3 • KN(SiMe3)2 • HF·Py • PPh3, DEAD • Ceric ammonium nitrate • Acetonitrile (solvent) • |