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Publication 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
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