CYCLIZATION AND REARRANGEMENT OF DITERPENOIDS. SYNTHESIS OF Δ12 - AND Δ13(14)-ISO-20-DEOXYLUTEONES

Article abstract of DOI:10.1007/BF00576213

Δ¹²- and Δ¹³⁽¹⁴⁾-Iso-20-deoxyluteones have been synthesized from 13E- and 13Z- bicyclogeranylgeranylacetones.The latter were reduced to the corresponding alcohols, which were acetylated, and the acetates obtained were cyclized with fluorosulfonic acid in nitropropane.The reaction product was saponified to a mixture of tricyclic alcohols which were oxidized with the chromium trioxide-pyridine complex to a mixture of Δ¹²- and Δ¹³⁽¹⁴⁾-iso-20-deoxyluteones and this was separated chromatographically.