Total synthesis of Mesembrane:
| Reference: | Pearson, W. H.; Szura, D. P.; Potich, M. J. J. Am. Chem. Soc. 1992, 114, 1329. DOI |
| Reactions: | CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+DMSO • Aldehyde → Imine • Azide → Amine • HWE → EneSulfide • Li/Sn → Li-Amine • Azaallyl anion Cycloaddition • Amine-5 • Cyclohexane • Bicyclo(430)-aza • Hydrogenolysis C-S • Alkyl-SR → Alkyl-H • Staudinger • |
| Reagents: | P(O)(OR)2CH2-SR' • AlH4-Li+ • DMSO, (COCl)2 (Swern) • PPh3 • RaNi • Me-Li • MeI • |