Total synthesis of Apiosporic Acid:
| Reference: | Gärtner, M.; Kossler, D.; Pflästerer, D.; Helmchen, G. J. Org. Chem, 2012, 77, 4491-4495. DOI |
| Reactions: | CarboxEster → Alkyl-OH • Julia-Kocienski • Li-Sulfone+Aldehyde • Sulfide → Sulfone • Mitsunobu → SR • Alkyl-X → Alkyl-SR • Pd/B-Alkyl+Vinyl-X • Diels-Alder, Intram, Ene • Cyclohexane • Bicyclo(440) • O-CPh3 → O-H • CarboxEster → CarboxAcid • Hydroboration → Alkyl-B • |
| Reagents: | Thiol, tetrazole • PBu3, DEAD • Mo7O24(NH4)6 • H2O2, Mo • Crotonaldehyde • KN(SiMe3)2 • BH-BBN • Vinyl-I • Acrylate • PdCl2(dppf) • AsPh3 • AlEt2-Cl • Hydroxide, sodium • Alkyl-BR2 • |