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

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