Total synthesis of Nitraraine:
| Reference: | Yamaguchi, R.; Hamasaki, T.; Sasaki, T.; Ohta, T. Utimoto, K.; Kozima, S.; Takaya, S. J. Org. Chem. 1993, 58, 1136. DOI |
| Reactions: | Sn-Allyl+Iminium • Iminium+Si-R • Diels-Alder, Intram, Ene • Lactam-6 • Bicyclo(440)-aza • Mg-Vinyl+Epoxide • Epoxide+Mg-R • Li-R → Sn-R • Li/H → Li-Allyl • N-C(O)R → N-CH2R • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • |
| Reagents: | Acryloyl-Cl • SiMe2tBu-Cl • AlH4-Li+ • Fluoride, R4N+ • Epoxide • Vinyl-MgX • BuLi(n) • SnMe3-Cl • Allyl-Li • TMEDA • |