Reference: | Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006, 128, 15960. DOI |
Keywords: | Mg-Vinyl+Aldehyde O-H → O-SiEt3 Ketal → Diol-1,2 Hydrostannation Alkyne Pd/Sn-Vinyl+Vinyl-X RCM → Lactone Lactone-9+ Claisen-Johnson Fritsch-Buttenberg-Wiechell Aldehyde → Alkyne Protecting group - Diene Sn-Vinyl → I-Vinyl CarboxEster → Aldehyde Si-Allyl+Aldehyde Aldehyde+Si-R Ether-5 O-H → O-SiEt3 Si-Alkyl → H-Alkyl Mg-Vinyl+Aldehyde Alkyl-OH → Aldehyde-α-OR Hydroboration alkene Alkyl-OH → Aldehyde Corey-Fuchs Ketal → Diol-1,2 B-Allyl+Aldehyde O-PMB → O-H Diol-1,2 cleavage |
Reagents: | DMSO, (COCl)2 (Swern) Vinyl-MgX Orthoacetate AlHiBu2 BH-BBN H2O2, NaOH DMSO, Py·SO3 (Parikh-Doering) PPh3=CBr2 BuLi(n) Acetic acid Periodate, sodium Vinyl-SiR3 Allyl-B(tartrate) Chiral auxiliary-Boronate SiEt3-Cl BF3·OEt2 Fluoride, R4N+ SiEt3-OTf DDQ Benzoyl chloride, 2,4,6-trichloro Ceric ammonium nitrate Grubbs I SnBu3-AlEt2 CuCN NIS Acetic acid Vinyl-SnR3 Pd(PPh3)4 CuCl Imidazole DMF (solvent) |