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Total synthesis of DMDA-Pat-A New:
Reference: Zhuo, C.; Furstner, A. Angew. Chem. Int. Ed. 2016, 55, 6051–6056. DOI
Keywords: O-H → O-SiPh2tBu • O-SiMe2tBu → O-H • Takai • Pd/Sn-Vinyl+Vinyl-X • Stille coupling • Wittig-ketomethyl → Enal • Hydroboration • Suzuki coupling • Yamaguchi • Pd-Sonogashira • Cu-Aryl+Allyl-X • Zn-Aryl → Cu-Aryl • Borylation Alkene • B-Alkyl → HO-Alkyl • Li-Alkynyl+Epoxide • Epoxide+Li-R • Alkyne → Vinyl-I • Alkyne → Vinyl-OAc • CarboxAcid → CarboxEster • Fe/Mg-Alkyl+Vinyl-X • Lactone-9+ • Takai-Utimoto → Vinyl-I •
Reagents: Zn° • CuCN • Allyl-Br • Pt(dba)3 • B2(Pinacol)2 • H2O2 • Hydroxide, sodium • 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 • MeMgBr • Bicarbonate, sodium • Fluoride, R4N+ • Acetic acid • DMSO, Py·SO3 (Parikh-Doering) • PPh3 • CrCl2 • Pd(PPh3)4 • NEtiPr2 • Pyridinium, 2-halo • CHI3

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