Total synthesis of Acerosolide:
| Reference: | Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165-169. DOI |
| Reactions: | CarboxEster → CarboxEster-α-SeR • Acetal(thio) → Aldehyde • Aldehyde → Alkyl-OH • CompRed-Aldehyde/CarboxEster+M-H • Pd/Sn-Vinyl+Benzyl-X • O-SiPh2tBu → O-H • Sn transmetalation • Allyl-OH → Allyl-Br • Appel → Br • Sn-Allyl+Aldehyde • Aldehyde+Sn-R • Benzyl-OH → Benzyl-Br • Nozaki-Hiyama coupling • Cr-Allyl+Aldehyde • Aldehyde+Cr-R • CompE+-Aldehyde/CarboxEster+M-R • Lactone-5 • Acetal(thio) → Acetal • Selenoxide-Ei → EneLactone • Lactone → EneLactone • Selenide → Selenoxide • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone • Lactone → Lactone-α-SeR • |
| Reagents: | Allyl-SnR3 • SnCl4 • Sulfonic acid, Camphor • KN(SiMe3)2 • SePh-Cl • AgClO4 • Periodate, sodium • BH4-Na+ • NBS • Pd(PPh3)4 • Vinyl-SnR3 • Br2 • HF • Cr2O7·2PyH (PDC) • Cr2O7·2PyH (PDC) • DMF (solvent) • Allyl-Br • CrCl2 • |