Total synthesis of Okinellin B:
| Reference: | Schmitz, W. D.; Messerschmidt, N. B. J. Org. Chem. 1998, 63, 2058. DOI |
| Reactions: | O-Bn → O-H • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Si-Alkynyl → H-Alkynyl • O-Bn → O-H • Takai-Utimoto → Vinyl-I • Mg-Alkyl+CarboxAmide • CarboxAmide(Weinreb)+Mg-R • Carboalumination Alkyne • Pd/Zn-Vinyl+Vinyl-X • CarboxEster(thio) enolate+Aldehyde • Lactone-4 • Mukaiyama Aldol • Aldol-Si • Ketene acetal+Aldehyde • Aldehyde+EnolSilane • Li/H → Li-Dithiane • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • CarboxEster → CarboxAmide(Weinreb) • Lactone-5 • CarboxEster → CarboxEster • Alkyl-OH → Aldehyde • Ketone → C=CH2 • Tebbe • Alkyl-OH → Aldehyde-α-OR • Ketal(thio) → CH2 • Ketone → CH2 • |
| Reagents: | RaNi • Ca°/NH3 • DMSO, (COCl)2 (Swern) • NHMe(OMe) • SiMe2tBu-Cl • Alkynyl-SiR3 • Alkyl-MgX • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • Ketene acetal • B(Cl)3 • AlMe3 • CHI3 • Pd2(dba)3 • Vinyl-Al • Vinyl-Al • ZnCl2 • BuLi(tert) • Tebbe • NMe(OMe)-AlMe2 • AlMe3 • |