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Total synthesis of Lucilactaene:
Reference: Coleman, R. S.; Walczak, M. C.; Campbell, E. L. J. Am. Chem. Soc. 2006, 127, 16038. DOI
Keywords: Alkyne Hydrostannation • Sn-Vinyl → I-Vinyl • Si-Vinyl → I-Vinyl • In-Allyl+CarboxAmide • O-H → O-SiEt3 • Cu-Vinyl+CarboxCl • CarboxCl+Cu-R • Vinyl-I → Vinyl-Mg • O-SiEt3 → O-H • N-SEM → N-H • Vinyl-Br → Vinyl-I • Pd/Sn-Vinyl+Aryl-X • CompNu-Sn-Vinyl/B-Vinyl+R-I • Stille coupling • Pd/B-Vinyl+Aryl-X • Suzuki coupling • Pd/Mg-Alkynyl+Vinyl-X • Kumada coupling • Silyl-metalation Alkyne • Allyl-OH → EnoateEster • Ozonolysis • Alkene cleavage • CompOx-Alkene/Enone+O3
Reagents: AIBN • I2 • Vinyl-I • Alkynyl-MgX • Pd(PPh3)4 • CuCN • MnO2 • NIS • Vinyl-I • Iodide, sodium • Allyl-In • DMF (solvent) • O3 • BH4-Na+ • SiEt3-OTf • Alkyl-MgX • CuCN • Acryloyl-Cl • Vinyl-Br • Vinyl-B • Vinyl-SnR3 • Pd2(dba)3 • AsPh3 • Vinyl-B • Pd(OAc)2 • Carbonate, sodium • Acetic acid, trifluoro •

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