First total synthesis of (+)-secosyrin 1

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2511-2512

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

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PLANT GLYCOSIDE; SECOSYRIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030942363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00380-8     Document Type: Article

References (12)

1. (a) Midland, S.L.; Keen, N.T.; Sims, J.J.; Midland, M.M.; Stayton, M.M.; Burton, V.; Smith, M.J.; Mazzola, E.P.; Graham, K.J.; Clardy, J. J. Org. Chem. 1993, 58, 2940.
2. (b) Midland, S.L.; Keen, N.T.; Sims, J.J. J. Org. Chem. 1995, 60, 1118.
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 1995, 32, 8809.
5. (c) Henschke, J.P.; Richards, R.W. Tetrahedron Lett. 1996, 37, 3557.
6. (d) Ishihara, J.; Sugimoto, T.; Murai, A. Synlett 1996, 335.
7. (e) Honda, T.; Mizutani, H.; Kanai, K. J. Org. Chem. 1996, 61, 9374.
8. Mukai, C.; Moharram, S.M.; Kataoka, O.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1995, 2849.
9. Compound 9 was efficiently converted into the 5-epimer of 11 by conventional means. X-Ray crystallographic analysis of the latter unambiguously established its stereochemistry, thereby the stereochemistry of 9 was confirmed. Details of X-ray analysis will be reported in somewhere else.
10. Nicholas K.M. Acc. Chem. Res. 20:1987;207.
11. No information on specific rotation of natural secosyrin 1 is available. b.
12. 3)]. This transformation combined with the details of this text will appear as a full paper in due course.