Total Synthesis of dl-Deguelin

Synthesis of Rotenoids V

Abstract

Starting with resorcinol, the total synthesis of dl-deguelin (VI) was accomplished. In the course of this investigation, dihydrodeguelic acid (II), dihydroisodeguelic acid (X), dihydrodehydrodeguelin (III), dehydrodeguelin (IV), dl-deguelol (V) and dihydro-β-rotenonone (XI) were prepared. But the reduction of dihydrodehydrodeguelin (III) to dihydrodeguelin (XII) resulted in failure. The preparation of dihydrodeguelol (XIIIa), its acetate (XIIIb) and dihydro-desoxy-Δ¹¹-dehydrodeguelin (XIV) was also described.