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Total synthesis of Brevisamide:
Reference: Herrmann, A.T.; Martinez, S.R.; Zakarian, A. Org. Lett. 2011, 13, 3636 DOI
Keywords: Corey-Fuchs • Vilsmeier formylation • Henry reaction • Nitro aldol • Achmatowicz rearrangement • Ether-6 • Pd/Sn-Vinyl+Aryl-X • Li-Alkynyl+Alkyl-X • Reductive etherification • ConjAdd Cu-R • Cu-Me+Enone • Enone+Cu-Me • Alkyne Silyl-metalation • Cu-SiR3+Alkyne • Allyl-OH → Enal • CompOx-Alcohol/Amine+Iodoso • Li-Alkynyl+Alkyl-X • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Nitro → Amine • N-H → N-C(O)R • Ketone → Alkyl-OH • Si-Vinyl → I-Vinyl •
Reagents: AlH4-Li+ • PPh3=CBr2 • POCl3 • Cu(OAc)2 • AlH4-Li+ • NBS • LiCuMe2 • BH4-Na+ • LiSiR3 • AsPh3 • TEMPO • DMSO, (COCl)2 (Swern) • BuLi(n) • Acetic anhydride • NIS • BF3·OEt2 • DMF (react) • MeNO2 • Iodosobenzene-OAc • Chiral catalyst •

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