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Total synthesis of Tetronolide (Part 1) New:
| Reference: | Boeckman, R. K. Jr.; Shao, P.; Wrobleski, S. T.; Boehmler, D. J.; Heintzelman, G. R.; Barbosa, A. J. J. Am. Chem. Soc. 2006, 128, 10572-10588. DOI (Part 2) (Part 3) |
| Reactions: | Li-R → Sn-R • Li/H → Li-Vinyl-OR • Li/Sn → Li-Vinyl • Li-Vinyl+CO2 • CarboxAcid → CarboxAmide • Alkene bromination • HWE → DienoateEster • Sharpless dihydroxylation • Alkene → Diol-1,2 • CompOx-Alkene/Enoate+OsO4 • Diol-1,2 cleavage • Enal → Allyl-OH • O-H → O-Alkyl • Williamson etherification • CarboxAmide → CarboxEster • Diels-Alder, Intram, Ene • Epoxidation, peracid • Epoxide → Allyl-OH • CarboxEster → CarboxAcid (tBu) • CarboxAcid → CarboxAnhydride • CarboxAnhydride → Alkyl-OH • O-H → O-SiMe2tBu • O-H/O-H+R3Si-X • O-H → O-MOM • Reductive elimination - X/OR • |
| Reagents: | BuLi, KOtBu • SnBu3-Cl • Vinyl-SnR3 • BuLi(n) • CO2 • O=C(OEt)Cl • Br2 • KOtBu • Fe(CN)6K3 • Carbonate, potassium • Sulfonamide, methane • Periodate, sodium • BH4-Na+ • Lutidine • Ti(OiPr)4 • Carbonate, potassium • BHT • Perbenzoic acid, 3-chloro • DBU • Acetic acid, trifluoro • O=C(OEt)Cl • NEt3 • BH4-Na+ • SiPh2tBu-Cl • DMAP • NEt3 • Chloromethyl ether • NEtiPr2 • Bicarbonate, sodium • Chiral auxiliary (amide) • BHT • |