Palladium[0]-mediated aminospirocyclization of tertiary allylic sulfones. Stereospecific construction of the azabicyclic ring system of cephalotaxine

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5253-5256

  Jin, Zhendong ^a   Fuchs, P L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHALOTAXINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030598010     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01112-4     Document Type: Article

References (13)

1. 1 Syntheses via vinyl sulfones 66.
2. 2 Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662.
3. 3 Jin, Z.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5205.
4. 4 Inami, H.; Ito, T.; Urabe, H.; Sato, F. Tetrahedron Lett. 1993, 34, 5919 and references cited therein.
5. 5 (a) Godleski, S. A.; Meinhart, J. D.; Miller, D. J.; Van Wallendael, S. Tetrahedron Lett. 1981, 22, 2247;
6. (b) Godleski, S. A.; Heacock, D. J.; Meinhart, J. D.; Van Wallendael, S. J. Org. Chem. 1983, 48, 2101;
7. (c) Carruthers, W.; Cumming, S. A. J.Chem.Soc. Chem. Commun. 1983, 360.
8. 6 (a) Trost, B. M.; Schmuff, N. R.; Miller, M. J. J. Am. Chem. Soc. 1980, 102, 5979;
9. (b) Mandai, T.; Matsumoto, T.; Tsuji, J. Synlett. 1993, 113 and references cited therein.
10. 7 Tertiary sulfones bearing the aminopropyl moiety were prepared via base-catalyzed phase transfer isomerative alkylation of the corresponding vinyl sulfones via reaction of acrylonitrile followed by nitrile reduction and reductive amination: See Jin, Z., Fuchs, P. L. Tetrahedron Lett. 1996, 37, 0000, preceding paper.
11. 8 Angyal, S. J.; Warburton, W. K. J. Chem. Soc. 1951, 2492.
12. 2 541.1957, found 541.1946.
13. 10 Z. Jin, unpublished results. The synthesis of derivative 11 will be eventually published in a subsequent full paper discussing the total synthesis of symchiral cephalotaxine 8. (formula presented)