image

Total synthesis of Acerosolide:
Reference: Paquette, L. A.; Astles, P. C. J. Org. Chem. 1993, 58, 165-169. DOI
Keywords: Lactone-5 • CarboxEster → CarboxEster-α-SeR • Acetal(thio) → Aldehyde • Aldehyde → Alkyl-OH • Pd/Sn-Vinyl+Benzyl-X • Stille coupling • O-SiPh2tBu → O-H • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone • Sn transmetalation • Selenoxide-Ei → EneLactone • Lactone → EneLactone • Allyl-OH → Allyl-Br • Sn-Allyl+Aldehyde • Aldehyde+Sn-R • Benzyl-OH → Benzyl-Br • Nozaki-Hiyama coupling • Cr-Allyl+Aldehyde • Aldehyde+Cr-R •
Reagents: Allyl-SnR3 • SnCl4 • Camphor sulfonic acid • KN(SiMe3)2 • SePh-Cl • AgClO4 • Periodate, sodium • BH4-Na+ • Me2S • Pd(PPh3)4 • Vinyl-SnR3 • Bromine • HF • Cr2O7·2PyH (PDC) • Cr2O7·2PyH (PDC) • DMF (solvent) • CrCl2

Syntheses Home