176. Synthesis of (–)-Pinidinevia asymmetric, electrophilic enolate hydroxyamination/nitrone reduction
     Oppolzer, W.; Merifield, E.
     Helv. Chim. Acta 1993, 76, 957-962

Enantiomerically pure(−)-pinidine (1) has been synthesized in 18.5% overall yield by a nine-step sequence starting from keto-ester 2. The key step 5 → 6 involves an asymmetric, electrophilic enolate hydroxyamination. Diastereoselective hydrogenation of nirtone 6 ensures thecis-relation between the substituents at C(2) and C(6) in piperidine 7.

DOI: 10.1002/hlca.19930760218 

open archive unige:85067