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Total synthesis of Iejimalide B (Part 2):
Reference: Schweitzer, D.; Kane, J. J.; Strand, D.; McHenry, P.; Tenniswood, M.; Helquist, P. Org. Lett. 2007, 9, 4619. DOI (Part 1)
Keywords: N-Boc → N-H • EnoateEster → Allyl-OH • Allyl-OH → Enal • Si-Alkynyl → H-Alkynyl • O-SiMe2tBu → O-H • Pd-Heck coupling • In-Allenyl/Propargyl+Enal • Enal+In-R • Pd/Sn-Vinyl+Vinyl-X • Stille coupling • Mechanism • CarboxAcid → CarboxAmide • Hydrostannation Alkyne • Lactone-9+ •
Reagents: Pd(OAc)2 • PPh3 • Acetic acid, trifluoro • AlHiBu2 • Dess-Martin • PPh3 • Pd(OAc)2 • InI • Carbonate, potassium • PdCl2(dppf) • HSnBu3 • Pd(PPh3)4 • CuCl • DMAP • TASF • NEt3 • DMSO (solvent) • DMF (solvent) •

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