Synthetie approaches to steroidal alkaloids III . An attempted synthesis of ring‐e of veratramine

In an effort to devise an alternative synthesis of the hydroxypiperidine ring present in the alkaloid veratramine, a model synthesis starting from cis ‐6‐phenyl‐4‐heptenoie acid was explored. This acid was converted to the epoxide of cis ‐6‐phcnyl‐1‐amino‐4‐hepten which on heating gave 2‐( 1‐hydroxy‐2‐phenylpropyl)pyrrolidine as the only produet. As a reference compound, 2‐(1‐phenylethyl)‐3‐hydroxypiperidine was synthesized using a variation of an established procedure.