Towards a total synthesis of ustiloxins A and B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1643-1646

  Hutton, Craig A ^a   White, Jonathan M ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANTIMITOTIC AGENT; CYCLOPEPTIDE; UNCLASSIFIED DRUG; USTILOXIN A; USTILOXIN B;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STEREOCHEMISTRY;

EID: 0031550848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00110-X     Document Type: Article

References (21)

1. 1. (a) Koiso, Y.; Li, Y.; Iwasaki, S. J. Antibiotics 1994, 47, 765-773.
2. (b) Koiso, Y.; Natori, M.; Iwasaki, S.; Sato, S.; Sonada, R.; Fujita, Y.; Yaegashi, H.; Sato, Z. Tetrahedron Lett. 1992, 33, 4157-4160.
3. 2. N-Boc-(S)-allylglycine (3) was obtained by protection of (S)-2-amino-4-pentenoic acid (Aldrich) under standard conditions, or via the procedure of Williams et al., see; Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547-1557.
4. 3. (a) Kurokawa, N.; Ohfune, Y. Tetrahedron 1993, 49, 6195-6222.
5. (b) Kurokawa, N.; Ohfune, Y. J. Am. Chem. Soc. 1986, 108, 6041-6043.
6. 4. Ohfune et al. (ref. 3) report an 8:1 ratio of cis-and trans-lactones 4a and 4b is obtained. Fusetani et al. reported that a 4:1 ratio of isomers is obtained under these conditions, as our results confirm, see; Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Wälchli, M. J. Am. Chem. Soc. 1989, 111, 2582-2588.
7. 3): δ 28.1, 35.2, 38.1, 51.0, 75.7, 80.3, 126.9, 129.0, 130.2, 134.3, 155.2, 174.3.
8. 6. (a) Brunel, J.-M.; Kagan, H. B. Synlett 1996, 404-406.
9. (b) Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
10. (c) Kagan, H. B.; Rebiere, F. Synlett 1990, 643-650.
11. (d) Zhao, S. H.; Samuel, O.; Kagan, H. B. Tetrahedron 1987, 43, 5135-5144.
12. 7. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325-326.
13. 8. (a) Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428-1437.
14. (b) Bulman Page, P. C.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. Synlett 1995, 773-775.
15. (c) Holland, H. L. Chem. Rev. 1988, 88, 473-485.
16. (d) Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 32, 9609-9618.
17. 9. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
18. 3): δ 28.2, 35.7, 50.9, 60.2, 71.6, 80.7, 124.0, 129.6, 131.7, 142.3, 155.2, 173.7.
19. 0 548 ; R 10.0652, wR2 = 0.1332.
20. 2O): δ 32.4, 49.1, 60.5, 72.7, 124.2, 130.0, 132.3, 141.7, 171.9.
21. 2O/TFA): δ 35.6, 50.4, 62.4, 63.4, 124.2, 129.8, 132.0, 141.1, 170.9.