Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8095-8103

  Mukai, Chisato ^a   Moharram, Sameh M ^a   Azukizawa, Satoru ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000044974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9711089     Document Type: Article

References (23)

1. (a) Smith, M. J.; Mazzola, E. P.; Sims, J. J.; Midland, S. L.; Keen, N. T.; Burton, V.; Staylon, M. M. Tetrahedron Lett. 1993, 34, 223.
2. (b) Midland, S. L.; Keen, N. T.; Sims, J. J.; Midland, M. M.; Staylon, M. M.; Burton, V.; Smith, M. J.; Mazzola, E. P.; Graham, K. J.; Clardy, J. J. Org. Chem. 1993, 58, 2940.
3. (a) Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286.
4. (b) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Komada, O. Tetrahedron Lett. 1995, 36, 3201.
5. (c) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Komada, O. Tetrahedron 1995, 32, 8809.
6. (d) Henschke, J. P.; Rickards, R. W. Tetrahedron Lett. 1996, 37, 3557.
7. (e) Ishihara, J.; Sugimoto, T.; Murai, A. Synlett 1996, 335.
8. (f) Honda, T.; Mizutani, H.; Kanai, K. J. Org. Chem. 1996, 61, 9374.
9. Midland, S. L.; Keen, N. T.; Sims, J. J. J. Org. Chem. 1995, 60, 1118.
10. The first total syntheis of (+)-secosyrin 1 (3) was reported as a preliminary communication: Mukai, C.; Moharram, S. M.; Hanaoka, M. Tetrahedron Lett. 1997, 38, 2511.
11. Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717.
12. Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226.
13. Steliou, K.; Poupart, M.-A. J. Org. Chem. 1985, 50, 4971.
14. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434.
15. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
16. Private communication from Professor J. J. Sims.
17. Fanton, E.; Gelas, J.; Horton, D. J. Chem. Soc., Chem. Commun. 1980, 21.
18. Mukai, C.; Moharram, S. M.; Kataoka, O.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1995, 2849.
19. Numbering for a 1,7-dioxaspiro[4.4]nonan-8-one skeleton was used for convenience.
20. Slomp, G., Jr.; Johnson, J. L. J. Am. Chem. Soc. 1958, 80, 915.
21. -1. A colorless prismatic crystal, ca. 0.1 ± 0.1 ± 0.15 mm, was mounted on a glass fiber. All measurements were made on a Rigaku AFC5R diffractometer. The cell dimensions and intensities were refined by the least-squares method, using 25 reflections on the diffractomer with Mo Kα radiation with w-scan mode for 20 less than 55.0°. The structure was solved by a direct method (MITHRIL method). The final cycle of full-matrix least-squares refinement was based on 2167 observed reflections. The final R value was 0.043.
22. Nicholas, K. M. Acc. Chem. Res 1987, 20, 207 and references therein.
23. The atomic coordinates for this structure have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.