Absolute configuration of scyphostatin

Organic Letters

Volumn 2, Issue 4, 2000, Pages 505-506

  Saito, Shoichi ^a   Tanaka, Natsuki ^a   Fujimoto, Katsumi ^a   Kogen, Hiroshi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001014891     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991351p     Document Type: Article

References (11)

1. (a) Tanaka, M.; Nara, F.; Suzuki-Konagai, K.; Hosoya, T.; Ogita, T. J. Am. Chem. Soc. 1997, 119, 7871.
2. (b) Nara, F.; Tanaka, M.; Hosoya, T.; Suzuki-Konagai, K.; Ogita, T. J. Antibiot. 1999, 52, 525.
3. (c) Nara, F.; Tanaka, M.; Masuda-Inoue, S.; Yamamoto, Y.; Doi-Yoshioka, H.; Suzuki-Konagai, K.; Kumakura, S.; Ogita, T. J. Antibiot. 1999, 52, 531.
4. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
5. Mori, K.; Kuwahara, S. Tetrahedron 1986, 42, 5539.
6. (a) Ungnade, H. E.; Nightingale, D. V. J. Am. Chem. Soc. 1944, 66, 1218.
7. (b) Mori, K.; Kuwahara, S. Tetrahedron 1986, 42, 5545.
8. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, L. B. J. Org. Chem. 1981, 46, 3938.
9. Clark, J. H.; Miller, J. M. Tetrahedron Lett. 1977, 599.
10. Another p-bromophenacyl ester, 11, was also obtained in 70% yield without epimerization. The compound was identical with an authentic sample, which was derived from 6 in two steps ((a) p-bromophenacyl bromide, KF, DMF (90%); (b) Dess-Martin oxidation (93%)). (formula presented)
11. (S)-(+)-2-Methylbutyric acid was purchased from Aldrich Chemical Co.