Enantioselective synthesis of (R)-1-azaspiro-[4.4]nonane-2,6-dione ethylene ketal, key chiral intermediate in the elaboration of (-)-cephalotaxine

Heterocycles

Volumn 66, Issue 1, 2005, Pages 31-37

  Pizzonero, Mathieu ^a   Dumas, Françoise ^a   d'Angelo, Jean ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33744489402     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(K)3     Document Type: Article

References (43)

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37. Value estimated on molecular model.
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41. (R)-8 (99% ee) is commercially available at low cost: 73.7per 100 g (0.825 mole) [Supplier: Acrós Organics, 2005].
42. Preparation of 3 according to ref. 5b required tedious separation of diastereomers by HPLC.
43. (S)-1-(1-naphthyl)ethylamine, the chiral inducer required for the synthesis of (S)-4 according to ref. 5e, is a very expensive chemical: 43.9per 1 g (0.0058 mole) [Supplier: Acrós Organics, 2005]. Furthermore, this inducer cannot be recovered, since further immolated through hydrogenolysis.