Baylis-Hillman protocol in an enantiocontrolled synthesis of pentenomycin I

Synlett

Volumn , Issue 4, 1999, Pages 419-420

  Sugahara, Tsutomu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Baylis Hillman reaction; Chiral building block; Chiral cyclopentadienone; Enantiocontrolled synthesis; Pentenomycin I

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; PENTENOMYCIN I; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0032928208     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2650     Document Type: Article

References (16)

1. a) Umino, K.; Furumai, T.; Matsuzawa, N.; Awataguchi, Y.; Ito, T.; Okuda,T. J. Antibiot. 1973,26, 506.
2. b) Umino, K.; Takeda, N.; Ito, Y.; Okuda, T. Chem. Pharm. Bull. 1974, 22, 1233.
3. c) Date, T.; Aoe, K.; Kotera, K.; Umino, K. Chem. Pharm. Bull. 1974, 22, 1963.
4. a) Smith, III, A. B.; Branca, S. J.; Pilla, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855.
5. b) Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1982, 23, 5463.
6. c) Hetmanski, M.; Purcell, N.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1984, 2089.
7. d) Pohmakotr, M.; Popuang, S. Tetrahedron Lett. 1991, 32, 275.
8. Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffatt, J. G. Pure Appl. Chem. 1978, 50, 1363.
9. A pertinent synthesis: Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101.
10. a) Ogasawara, K. Pure Appl. Chem. 1994, 66, 2119.
11. b) Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 15.
12. Pertinent reviews, see: a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
13. b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
14. Rezgni, F.; Elgaied, M. M. Tetrahedron Lett. 1998, 39, 5965.
15. Takano, S; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359.
16. 2c].