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) |