Total synthesis of Dihydrocompactin (partial) (Burke):
| Reference: | Burke, S. D., Saunders, J. O.; Oplinger, J. A.; Murtiashaw, C. W. Tetrahedron Lett., 1985, 26, 1131. DOI |
| Reactions: | CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Aldehyde+Mg-Vinyl • Jones oxidation • Aldehyde → CarboxAcid • CarboxAcid → CarboxCl • Claisen-Ireland • Claisen-EnolEther • Wittig-methoxymethyl • Reductive formylation • Cationic cyclization • Cyclohexene • Bicyclo(440) • Si-Vinyl+Carbenium • Li-SiR3+Aldehyde • Enal+Li-R • Li-PhosphineOxide+CarboxCl • Jones oxidation • Mechanism • O-H → O-C(O)R • Ketone → Alkyl-OH • |
| Reagents: | Crotonaldehyde • SiR3-Li • LiNiPr2 • SiMe2tBu-Cl • Diazomethane • AlH4-Li+ • CrO3·Py2 (Collins) • Vinyl-MgX • Vinyl-OR • Hg(OC(O)CF3)2 • PPh3=CH-OR • CrO3, H2SO4 (Jones) • Oxalyl chloride • BH(sBu3)-K+ • P(O)Ph2CH2-R • AlHiBu2 • NaH • CrO3, H2SO4 (Jones) • SbCl5 • |