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Total synthesis of Stipiamide, 6,7-Dehydro:
Reference: Zeng, X.; Zeng, F.; Negishi, E. Org. Lett. 2004, 6, 3245-3248. DOI
Keywords: Alkyl-OH → Aldehyde • O-SiMe2tBu → O-H • Peterson → Enal • Aldehyde azaenolate+Aldehyde • Corey-Fuchs • Pd/Zn-Alkynyl+Vinyl-X • B-Allyl-Ipc+Aldehyde • Carboalumination Alkene • Alkyne Hydrozirconation • Fritsch-Buttenberg-Wiechell • CarboxAcid → CarboxAmide • Al-Alkyl → HO-Alkyl • O-H → O-SiMe2tBu • Alkene → Diol-1,2 • Diol-1,2 cleavage • Zr-Vinyl → X-Vinyl • Li/Br → Li-Vinyl • Li-R → Zn-R • Pd/Zn-Alkynyl+Vinyl-X • Pd/Zn-Vinyl+Vinyl-X • Si-Alkynyl → H-Alkynyl • Li/H → Li-Alkynyl • Li-R → Zn-R • CarboxAcid → CarboxEster •
Reagents: Chiral catalyst • AlMe3 • O2 • DMSO, (COCl)2 (Swern) • BuLi(sec) • Acetic acid, trifluoro • SiMe2tBu-Cl • AD-Mix • Periodate, sodium • BuLi(sec) • Acetic acid, trifluoro • PPh3=CBr2 • BuLi(n) • ZrCp2ClH • I2 • PdCl2(PPh3)2 • Fluoride, R4N+ • NEtiPr2 • Alkynyl-ZnX • Chiral auxiliary-Boronate • Vinyl-Zr • Crotyl-B(Ipc)2 • Hydroxide, lithium • Alkynyl-ZnX • Vinyl-I • Ethylene dibromide • Pd(PPh3)4 • Alkynyl-SiR3 • Vinyl-ZnX • BuLi(tert) • Methacrylate • Vinyl-Br • Carbonate, potassium • Alkynyl-ZnX • PdCl2(PPh3)2 • LiNiPr2

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