Total synthesis of Agelastatin A:
| Reference: | Davis, F. A.; Deng J. Org. Lett. 2005, 7, 621. DOI Davis, F. A.; Zhang, J.; Zhang, Y. Qiu, H. Syn. Commun. 2009, 39, 1914. DOI |
| Reactions: | N-SO2R → N-H • Sulfinamide, chiral • CarboxEster enolate+Imine • Imine+Enolate • Aryl-H → Aryl-Br • N-H → N-C(O)NR2 • ConjAdd Amine • Lactam-6 • CarboxAmide(Weinreb)+Mg-R • Mg-Allyl+CarboxAmide • RCM → Ring-C • Cyclopentenone • N-Bn → N-H • CarboxEster → CarboxAmide(Weinreb) • Alkene isomerization • CarboxAcid → CarboxEster • |
| Reagents: | LiNiPr2 • Sulfinamide • LiN(OMe)Me • Acetic acid, trifluoro • Allyl-MgX • HBTU • Chiral auxiliary (sulfinamide) • Grubbs II • Carbonate, cesium • H2, Pd • Isocyanate • NEt3 • |