Total Syntheses

Reaction scheme for total synthesis of the natural product Psymberin (Partial)
Total synthesis of Psymberin (Partial):
Reference:Rech, J. C.; Floreancig, P. E. Org. Lett. 2005, 7, 5175-5178. DOI
Reactions:Ether-6 • Diels-Alder, Allene • B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • Benzene synthesis • Ozonolysis • Ozonolysis • Mukaiyama Aldol • Aldol-Si • Aldehyde+EnolSilane • Felkin-Anh • CarboxEster → Aldehyde • CompRed-CarboxEster/CarboxEster+M-H • Ketone → Alkyl-OH • Felkin-Anh • Cyanohydrin • O-H → O-C(O)R • O-C(O)R → O-H • Lactone-6 • O-SiMe2tBu → O-H (phenol) • O-H → O-SiMe2tBu • O-H → O-SiMe2tBu (phenol) • O-H → O-SiEt3 • Ketone → EnolSilane • Si-Allyl+Aldehyde • Aldehyde+Si-R • CompE+-Aldehyde/Ketone+Si-Allyl •
Reagents:Allene dicarboxylate • Butadiene, 2-OR • HF·NEt3 • SiMe2tBu-OTf • AlHiBu2 • Chiral auxiliary (boronate) • SiMe2tBu-OTf • O3 • BF3·OEt2 • BH4-Na+ • O3; PPh3 • Cyanide, trimethylsilyl • Acetic anhydride, Py • Fluoride, R4N+ • Carbonate, potassium • Crotyl-B(Ipc)2 • Lutidine • BF3·OEt2 • Lutidine • Allyl-SiR3 • Chiral auxiliary (misc) • SiEt3-Cl • SiMe3-OTf • NEt3 •