Total synthesis of Rhyzoxin D (Burke):
| Reference: | Jiang, Y.; Hong, J.; Burke, S. D. Org. Lett. 2004, 6, 1445. DOI |
| Reactions: | Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • Aldol-B-Ipc • Ketone → EnolBorane • CarboxAmide(Weinreb) → Aldehyde • O-H → O-Me • CarboxAmide(Evans) → CarboxAmide(Weinreb) • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • O-H → O-SiEt3 • RCM → Ring-C • Cyclopentene • Sulfide → Sulfone • Mitsunobu → SR • Alkyl-X → Alkyl-SR • Alkene → Diol-1,2 • O-H → O-SiEt3 • Carboxamide(Evans) → Alkyl-OH • O-H → O-SiiPr3 • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Meerwein-Ponndorf-Verley • Evans-Tishchenko reduction • Julia-Kocienski • Li-Sulfone+Aldehyde • O-H → O-C(O)R • Allyl-OH → Enal • O-PMB → O-H • HWE → EnoateEster (intram) • Lactone-9+ • Mechanism • Lactone-6 • O-C(O)R → O-H • O-H → O-C(O)R • O-SiEt3 → O-H • Diol-1,2 cleavage • Lactol → Lactone • Lactone-6 • Allyl-OH → Enal • O-SiiPr3 → O-H • HWE → Diene • |
| Reagents: | B(OTf)Bu2 • Chiral auxiliary (amide-Evans) • NHMe(OMe) • MeI • AlHiBu2 • B(Cl)(Ipc)2 • Chiral auxiliary (amide-Evans) • Chiral auxiliary (boronate) • AlMe3 • NMe(OMe)-AlMe2 • Grubbs I • Chiral auxiliary (amide-Evans) • B(OTf)Bu2 • Chiral auxiliary (amide-Evans) • Lutidine • OsO4, NMO • SiEt3-OTf • BH4-Li+ • Thiol, benzothiazole • Perbenzoic acid, 3-chloro • PPh3, DEAD • SmI2 • SiiPr3-OTf • HF·Py • Dess-Martin • LiCHR-Sulfonyl • LiN(SiMe3)2 • 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 • P(O)(OR)2CH2-Vinyl • KOtBu • HF·Py • B(Cl)(Ipc)2 • |