| 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 |