-boeckman.gif)
Total synthesis of Tetronolide (Part 2) 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 1) (Part 3) |
| Reactions: | O-PMB → O-H • O-SiMe2tBu → O-H • Li/H → Li-Alkynyl • Li-Alkynyl+Aldehyde • Alkyne → Ene-trans • Hydroalumination Alkyne • Allyl-X → Allyl-PRn • CarboxAmide enolate+Alkyl-X • Allyl-X+Enolate (asym) • CarboxAmide → Alkyl-OH • O-H → O-SiMe2tBu • Sharpless epoxidation • O-H → O-Bn • Al-Alkyl+Epoxide • Epoxide+Al-R • Li-R → Al-R • O-H → O-MOM • O-Bn → O-H • Alkyl-OH → Aldehyde • Li-PhosphineOxide+Aldehyde • Alkyl-OH → Aldehyde • HWE → DienoateEster • Allyl-OH → Allyl-Cl • |
| Reagents: | LiNiPr2 • Allyl-I • AlH4-Li+ • SiPh2tBu-Cl • Imidazole • DDQ • Hydroperoxide, tbutyl • Tartrate, diethyl • Ti(OiPr)4 • Benzyl-X • KH • Iodide, R4N+ • AlMe3 • BuLi(n) • Chloromethyl ether • NEtiPr2 • Iodide, R4N+ • H2, Pd • DMSO, (COCl)2 (Swern) • NEtiPr2 • DMSO, (COCl)2 (Swern) • NEtiPr2 • Fluoride, R4N+ • LiNiPr2 • HMPA (solvent) • BuLi(n) • Formaldehyde • AlH4-Li+ • NCS • Me2S • BuLi(n) • Chiral auxiliary (amide) • |