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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
Keywords: Allyl-OH → Enone • Chelotropic, SO2 • Protecting group - Diene • EnoateEster → Allyl-OH • Allyl-OH → Enone • Ketone → Alkyl-OH • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Diol-1,2 cleavage • Diol-1,2 → Carbonate • Epoxidation, V • Epoxide → Allyl-OH • Grob fragmentation • O-H → O-Me • Sn-Allenyl+Aldehyde • Aldehyde+Sn-R • Sn-Allenyl+Aldehyde • Enal+Sn-R • Epoxidation, V • Epoxidation, V • Epoxide → Diol • Furan synthesis • Ketone-α-OR → Ketone • Diels-Alder, Intram • Ether-5 • Diels-Alder, Allene • Furan-cycloaddition •
Reagents: Allenyl-SnR3 • SnCl2 • Dess-Martin • AgNO3 • SnCl2 • AlHiBu2 • Permanganate, barium • AlHiBu2 • Hydroperoxide, tbutyl • SiMe2tBu-OTf • Hydroxide, sodium • Periodate, sodium • SmI2 • O=CCl2 • Hydroperoxide, tbutyl - VO(acac)2 • NEt3 • Carbonate, potassium • MeI • VO(acac)2 • Carbonate, calcium • Ag2O •

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