Total Syntheses

Reaction scheme for total synthesis of the natural product Vitamin A
Total synthesis of Vitamin A:
Reference:Julia, M.; Arnould, D. Bull. Soc. Chim. Fr.. 1973, 746
Reactions:Li-Sulfone+Alkyl-X • Allyl-X+Li-R • CompE+-Allyl-Br/CarboxEster+M-R • Mg-Vinyl+Ketone • Enone+Mg-R • Dehydrosulfonylation → Diene • Allyl-OH → Allyl-Br • Allyl-X → Allyl-SO2R • CarboxEster → CarboxAcid •
Reagents:Vinyl-MgX • PBr3 • LiCHR-Sulfonyl • KOtBu • Allyl-Br • Sulfinate, benzene • Hydroxide, potassium •