Total synthesis of DMDA-Pat-A:
| Reference: | Zhuo, C.; Furstner, A. Angew. Chem. Int. Ed. 2016, 55, 6051–6056. DOI |
| Reactions: | Takai-Utimoto → Vinyl-I • CompE+-Aldehyde/CarboxEster+M-R • Pd/Sn-Vinyl+Vinyl-X • Wittig-ketomethyl → Enal • CompE+-Aldehyde/CarboxEster+Wittig • Hydroboration → Alkyl-B • Pd/B-Alkyl+Aryl-X • O-H → O-C(O)R • Pd/H-Alkynyl+Vinyl-X • Cu-Aryl+Allyl-X • Zn-R → Cu-R • CompRed-Aryl-Br/Aryl-Br+M° • Borylation Alkene • Pd/B-B+Alkene • B-Alkyl → HO-Alkyl • Li-Alkynyl+Epoxide • Epoxide+Li-R • Alkyne → Vinyl-I • Alkyne → Vinyl-OAc • CarboxAcid → CarboxEster • Fe/Mg-Alkyl+Vinyl-X • Mg-R → Fe-R • CarboxAcid → CarboxEster • Lactone-9+ • O-H → O-SiPh2tBu • CompNu-O-H/O-H+R3Si-X • O-SiMe2tBu → O-H • Pyrone synthesis • |
| Reagents: | Epoxide • Propiolate • Acrylate • Vinyl-I • Zn° • CuCN • Allyl-Br • Pt(dba)3 • B2(Pinacol)2 • Chiral catalyst (phosphine) • H2O2, NaOH • SiPh2tBu-Cl • DMAP • NEt3 • Alkynyl-Li • Iodide, sodium • Acetic acid • Pd(PPh3)4 • CuI • NEt3 • AuNTf2 • Benzoyl chloride, 2,4,6-trichloro • NEt3 • DMAP • BH-BBN • Pd(OAc)2 • Fe(acac)3 • Me-MgBr • Bicarbonate, sodium • Fluoride, R4N+ • Acetic acid • DMSO, Py·SO3 (Parikh-Doering) • PPh3=C(Me)-C(O)R • CHI3 • Vinyl-SnR3 • Pd(PPh3)4 • Alkyl-BR2 • NEtiPr2 • Pyridinium, 2-halo • |