Total synthesis of Nitidasin (Part 2) New:
| Reference: | Daniel T. Hog, D.T.; Florian M. E. Huber, F. M. E.; Peter Mayer, P.; Trauner, D. Angew. Chem. Int. Ed. 2014, 53, 8513-8517 DOI (Part 1) |
| Reactions: | Epoxidation, peracid • Alkene cleavage • Epoxide → Diol • Diol-1,2 cleavage • Corey-Fuchs • Fritsch-Buttenberg-Wiechell • Li-Alkynyl+Alkyl-X • Hydrozirconation Alkyne • Hydrozirconation Alkene • Cyclopentane • Dehydrohalogenation → Ene • Hydroboration → Alkyl-OH • Alkyl-OH → Aldehyde • Wittig-methyl • Li/I → Li-Vinyl • Ketone+Li-Vinyl • Epoxidation, peracid • RCM → Ring-C • Cyclooctane • O-SEM → O-H • Hydrogenation Alkene • Alkyl-OH → Ketone • |
| Reagents: | Perbenzoic acid, 3-chloro • Periodic acid • BuLi(n) • MeI • ZrCp2Cl2 • BuLi(n) • NIS • DBU • BH-BBN • H2O2, NaOH • DMSO, (COCl)2 (Swern) • NEt3 • PPh3=CH2 • BuLi(tert) • Perbenzoic acid, 3-chloro • Grubbs II • TASF • H2, Pd • RuO4-Pr4N+ • NMO • PPh3=CBr2 • PPh3, CBr4 • |