Total synthesis of Prelog Djerassi Lactone:
| Reference: | Risi, R. M.; Burke, S. D. Org. Lett., 2012, 14, 2572–2575. DOI |
| Reactions: | CarboxEster → CarboxAcid • Orthoester → CarboxEster • Hydrogenation EnoateEster (asym) • Lactone-6 • Hydroformylation • B-Allyl+Aldehyde • Ozonolysis • Wittig-carboxymethyl → EnoateEster • CarboxAcid → CarboxEster • |
| Reagents: | CO, H2 • Allyl-BR2 • Chiral auxiliary (boronate) • O3 • PPh3 • PPh3=C(Me)-CO2R • Rh(cod)Cl • H2, Rh • Acetic acid • Hydroxide, lithium • Diazomethane, silyl • BINAP • |