Total synthesis of Psiguadial B:
| Reference: | Chapman, L. M.; Beck, J. C.; Wu, L.; Reisman. S. E. J. Am. Chem. Soc. 2016, 138, 9803-9806. DOI |
| Reactions: | Diazoketone → Ketene • Cyclobutane • Ketene+Amine (asym) • Pd/H-C+Vinyl-X • CarboxAmide → Aldehyde • Aldehyde epimerization • Ketal → Ketone • Alkene isomerization • Wittig-methyl • Aldol-Na → Enone • Li-Vinyl+Ketone • Ketone+Li-Vinyl • RCM → Ring-C • Bicyclo(431) • Bicyclo(520) • Hydrogenation Alkene • Aryl-Br → Aryl-OR • O-H → O-Alkyl (phenol) • Ether-6 • Bicyclo(440)-oxa • Benzylic oxidation → Benzyl-OR • Cu-Aryl+Alkyl-X • Alkyl-X+Cu-R • O-Me → O-H (phenol) • Friedel-Crafts Acylation • Aryl-H → Aryl-CHO • Cu-Me+Enone • Al-R → Cu-R • ConjAdd Cu-R (asym) • |
| Reagents: | Pd(OAc)2 • Ag2CO3 • ZrCp2ClH • Hydroxide, potassium • PPh3=CH2 • HCl, H2O • AlMe3 • Hydroxide, potassium • Vinyl-Li • Grubbs II • H2, Ir • Crabtree catalyst • CuI • KOtBu • DDQ • BF3·OEt2 • Cl2CH-OMe • TiCl4 • Chiral catalyst (amino-alcohol) • Crabtree catalyst • Cinchonidine • |