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Total synthesis of Rhyzoxin D:
Reference: Jiang, Y.; Hong, J.; Burke, S. D. Org. Lett. 2004, 6, 1445. DOI
Keywords: O-H → O-SiiPr3 • O-SiMe2tBu → O-H • O-PMB → O-H • O-SiiPr3 → O-H • Aldol-B-Evans • HWE → Diene • Aldol-B-Ipc • Ketone → EnolBorane • HWE → EnoateEster (intram) • Lactone-9+ • Meerwein-Ponndorf-Verley • CarboxAmide(Weinreb) → Aldehyde • Evans-Tishchenko reduction • Mechanism • Lactone-6 • Aldol-B-Evans • O-H → O-SiEt3 • Sulfide → Sulfone • RCM → Ring-C • Cyclopentene • Mitsunobu → SR • Alkyl-X → Alkyl-SR • Julia-Kocienski • Li-Sulfone+Aldehyde • Alkene → Diol-1,2 • O-H → O-SiEt3 • Carboxamide(Evans) → Alkyl-OH • O-H → O-Me • CarboxAmide(Evans) → CarboxAmide(Weinreb) • O-H → O-C(O)R • O-PNBz → O-H • O-H → O-C(O)R • O-SiEt3 → O-H • Diol-1,2 cleavage • Lactol → Lactone • Lactone-6 • Allyl-OH → Enal • Allyl-OH → Enal •
Reagents: BOTfBu2 • P(O)(OR)2CH2-Vinyl • KOtBu • 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-C(O)OR' • DBU • DDQ • MnO2 • HF·Py • Chiral auxiliary-Boronate • NMe(OMe)-H • Grubbs I • BOTfBu2 • Lutidine • OsO4, NMO • SiEt3-OTf • BH4-Li+ • Thiol, benzothiazole • Perbenzoic acid, 3-chloro • PPh3, DEAD • LiCHR-Sulfonyl • LiN(SiMe3)2 • BCl(Ipc)2

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