Total synthesis of Lineatin:
| Reference: | Baeckstrom, P.; Li, L.; Polec, I.; Unelius, C. R.; Wimalasiri, W. R. J. Org. Chem. 1991, 56, 3358. DOI |
| Reactions: | Alkene isomerization • HWE → EnoateEster • Claisen-EnolEther • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Mechanism • Ketene Cycloaddition • Cyclobutane • Cyclopentene • Bicyclo(320) • CarboxAcid → Ketene • Ketene synthesis • Ether-6 • CarboxEster → CarboxAcid • Ketone → Alkyl-OH • O-H → O-C(O)R • Alkene → Diol-1,2 • Diol-1,2 cleavage • Alkene cleavage • Aldehyde → Acetal(Me) • Acetal → Aldehyde • Ether-6 • |
| Reagents: | Me2C(OMe)2 • Formic acid • Hydroxide, potassium • Pd/C • AlH4-Li+ • Acetic anhydride, Py • OsO4 • Periodic acid • HOMe (react) • Me-MgBr • HCl, H2O • Acetate, sodium • P(O)(OR)2CH2-C(O)OR' • |