Abstract
AbstractThe synthesis of three 9,11‐dideoxyprostaglandins in which the cyclopentane moiety is replaced by a six‐membered ring, is described. Starting from phthalaldehydic acid (1) the aromatic PG‐analogue, 7‐[2‐(3‐hydroxy‐(E)‐1‐octenyl)phenyl]heptanoic acid (9), was prepared in 7 steps in 49% overall yield. The cis‐substituted cyclohexane PG‐analogue, ethyl 7‐[cis‐2‐(3‐hydroxy‐(E)‐1‐octenyl)cyclohexyl]heptanoate (34), was obtained in 7 steps in 53% overall yield from the same starting material 1. The trans‐substituted cyclohexane PG‐analogue, ethyl 7‐[trans‐2‐(3‐hydroxy‐(E)‐1‐octenyl)cyclohexyl]heptanoate (20), was synthesized from methyl 9‐cyano‐(E)‐2‐nonenoate (12) in 8 steps in 34% yield.
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