Total synthesis of Eleutherobin Model:
| Reference: | Winkler, J. D.; Quinn, K. J.; MacKinnon, C. H.; Hiscock, S. D.; McLaughlin, E. C. Org. Lett. 2003, 5, 1805. DOI |
| Reactions: | Chelotropic, SO2 • Protecting group - Diene • O-SiMe2tBu → O-H • Epoxidation, V • CompOx-Alkene/Alkene+M-OOR • Grob fragmentation • Bicyclo(840) • Sn-Allenyl+Aldehyde • Aldehyde+Sn-R • Allene synthesis • Sn-Allenyl+Aldehyde • Enal+Sn-R • Allene synthesis • Epoxidation, V • Epoxide → Diol • Epoxide+M-OR • Furan synthesis • Ketone-α-OR → Ketone • Diels-Alder, Intram, Allene • Cyclohexanone • Bicyclo(440) • Diels-Alder, Allene • Furan cycloaddition • Ether-5 • Bicyclo(221)-oxa • Allyl-OH → Enone • EnoateEster → Allyl-OH • Allyl-OH → Enone • Diol-1,2 cleavage • O-H → O-SiMe2tBu • Ketone → Alkyl-OH • Epoxidation, V • CompOx-Alkene/Alkene+M-OOR • Epoxide → Allyl-OH • O-H → O-Me • Diol-1,3 → Carbonate • Carbonate → Diol-1,3 • |
| Reagents: | Propargyl-Br • SnCl2 • Dess-Martin • AgNO3 • Butadiene • SnCl2 • AlHiBu2 • Permanganate, barium • AlHiBu2 • Hydroperoxide, tbutyl - V • SiMe2tBu-OTf • Hydroxide, sodium • Periodate, sodium • SmI2 • O=CCl2 • Hydroperoxide, tbutyl - V • NEt3 • Carbonate, potassium • MeI • Carbonate, calcium • Ag2O • SO2 • |