1-Azaspiro[4.4]nonane-2,6-dione and the separation and absolute configurations of its enantiomers

Tetrahedron Asymmetry

Volumn 8, Issue 2, 1997, Pages 191-194

  Nagasaka, Tatsuo ^a   Sato, Hiroto ^a   Saeki, Shin Ichiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOTAXINE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031035588     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00509-5     Document Type: Article

References (10)

1. Kuehne, M. E.; Bornmann, W. G.; Parsons, W. H.; Spitzer, T. D.; Blount, J. F.; Zubieta, J. J. Org. Chem. 1988, 53, 3439.
2. +). mp 96-98C°.
3. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 55, 207.
4. 2O (10:0.1:1) (12 h), respectively. (matrix presented)
5. HPLC analysis was kindly carried out by Dr. Yasuo Dobashi, Tokyo University of Pharmacy and Life Science, using a chiral column (cited in Figure 1) prepared by himself. cf. Dobashi, Y.; Hara, S. J. Org. Chem. 1987, 52, 2490.
6. Kajtar, M.; Hollose, M.; Kinsky, K.; Majer, Z. Coll. Czech. Chem. Commun. 1982, 47, 950. (matrix presented) (R)-(+)1,7-diazaspiro-(S)-(-)-1,7-diazaspiro-[4.4]nonane-2,6-dione [4.4]nonane-2,6-dione
7. -3, Absorption Coefficient: none.: Authors thank Mr. Tadashi Hata, Sankyo Co. Ltd., for the X-ray analysis of (+)-8.
8. The direct alkylation of amides {(+)-1 and (-)-1} with alkyl halides in the presence of bases and phase transfer catalysts was not conducted successfully. For the alkylation of (+)-8 and (-)-9 to (+)-10 and (-)-10, respectively, tosylate (in Scheme 2) was better than any corresponding alkyl halide.
9. 3). Synthesis of (-)-cephalotaxine has recently been reported: Isono, N.; Mori, M. J. Org. Chem. 1995, 60, 115.
10. Arona, S. K.; Bates R. B.; Grady, R. A. J. Org. Chem. 1974, 39, 1269.