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Total synthesis of Rhyzoxin D:
Reference: Jiang, Y.; Hong, J.; Burke, S. D. Org. Lett. 2004, 6, 1445. DOI
Keywords: CarboxAmide(Evans) -> CarboxAmide(Weinreb) • O-H -> O-Me • O-H -> O-PNBz • O-H -> O-SiiPr3 • O-SiMe2tBu -> O-H • Allyl-OH -> Enal • O-PNBz -> O-H • Diol-1,2 cleavage • Lactol -> Lactone • Lactone-6 • O-PMB -> O-H • Allyl-OH -> Enal • O-SiiPr3 -> O-H • Aldol-B-Evans • HWE -> Diene • Aldol-B-Ipc • HWE -> EneLactone • Lactone-15+ • Meerwein-Ponndorf-Verley • CarboxAmide(Weinreb) -> Aldehyde • Evans-Tishchenko reduction • Mechanism • Lactone-6 • Aldol-B-Evans • O-H -> O-SiEt3 • Alkene -> Diol-1,2 • O-H -> O-SiEt3 • Carboxamide(Evans) -> Alkyl-OH • Sulfide -> Sulfone • RCM -> Ring-C • Mitsunobu -> SR • Julia-Kocienski • Chiral auxiliary •
Reagents: BOTfBu2 • P(O)(OR)2CH2-Vinyl • AlMe3 • MeI • AlHiBu2 • BCl(Ipc)2 • SmI2 • SiiPr3-OTf • HF·Py • Dess-Martin • AlHiBu2 • P(O)(OR)2CH2-C(O)Cl • Acetic acid • Periodate, sodium • RuO4-Pr4N+, NMO • P(O)(OR)2CH2-CO2R • DBU • DDQ • MnO2 • HF·Py • NMe(OMe)-H • BOTfBu2 • OsO4, NMO • SiEt3-OTf • BH4-Li+ • Perbenzoic acid, 3-chloro • PPh3, DEAD • LiCHR-Sulfonyl • LiN(SiMe3)2

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