Synthesis and absolute stereochemisty of a cruciferous phytoalexin, (-)-spirobrassinin

Chemistry Letters

Volumn , Issue 8, 2000, Pages 886-887

  Monde, Kenji ^a   Osawa, Shuichi ^a   Harada, Nobuyuki ^a   Takasugi, Mitsuo ^b   Suchy, Mojmir ^c   Kutschy, Peter ^c   Dzurilla, Milan ^c   Balentova, Eva ^c  

^a TOHOKU UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c P J AFÁRIK UNIVERSITY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034354468     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.886     Document Type: Article

References (20)

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2. b) C. J. W. Brooks and D. G. Watson, Nat. Prod. Rep., 8, 427 (1991).
3. a) M. Tukusugi, N. Katsui, and A. Shirata, J. Chem. Soc., Chem. Commun., 1986, 1077.
4. b) M. Takasugi, K. Monde, N. Katsui, and A. Shirata, Bull. Chem. Soc. Jpn., 61, 285 (1988).
5. Recent Review: M. S. C. Pedras, F. I. Okanga, I. L. Zaharia, and A. Q. Khan, Phytochemistry, 53, 161 (2000).
6. For antimicrobial activity, see ref. 3. For antitumor activity, see R. G. Mehta, J. Liu, A. Constantinou, M. Hawthorne, J. M. Pezzuto, R. C. Moon, and R. M. Moriarty, Anticancer Res., 14, 1209 (1994). For oviposition stimulant activity, see R. Baur, E. Städler, K. Monde, and M. Takasugi, Chemoecology, 8, 163 (1998).
7. For antimicrobial activity, see ref. 3. For antitumor activity, see R. G. Mehta, J. Liu, A. Constantinou, M. Hawthorne, J. M. Pezzuto, R. C. Moon, and R. M. Moriarty, Anticancer Res., 14, 1209 (1994). For oviposition stimulant activity, see R. Baur, E. Städler, K. Monde, and M. Takasugi, Chemoecology, 8, 163 (1998).
8. M. S. C. Pedras and J. L. Sorensen, Phytochemistry, 49, 1959 (1998).
9. M. Takasugi, K. Monde, N. Katsui, and A. Shirata, Chem. Lett., 1987, 1631.
10. K. Monde, N. Harada, M. Takasugi, P. Kutschy, M. Suchy, and M. Dzurilla, J. Nat. Prod., submitted (2000).
11. K. Monde, K. Sasaki, A. Shirata, and M. Takasugi, Phytochemistry, 30, 2915 (1991).
12. K. Monde, M. Takasugi, and T. Ohnishi, J. Am. Chem. Soc., 116, 6650 (1994).
13. 3) δ 179.1, 164.0, 150.6, 142.8, 139.2, 130.1, 128.8, 128.3, 127.5, 126.0, 125.6, 123.7, 116.6, 75.6, 65.5, 50.1, 22.7, 15.7.
14. The enantiomeric excesses were determined by HPLC analysis using a Sumichiral OA-4700 chiral column (i-PrOH-dichloroethane-hexane 2:8:90) monitoring by photodiode array and HPLC-CD detectors.
15. ext (Δε) 204.4 (-21.0), 221.0 (25.9), 240.0 (-2.6), 248.8 (1.0), 263.6 (-5.9), 308.2 (-5.1) nm.
16. 3).
17. a) N. Harada and K. Nakanishi, "Circular Dichroic Spectroscopy -Exciton Coupling in Organic Stereochemistry," University Science Books, Mill Valley (1983).
18. b) K. Nakanishi and N. Berova, in "Circular Dichroism -Principles and Applications," ed. by K. Nakanishi, N. Berova, and R. W. Woody, VCH Publishers, New York (1994), p. 361.
19. 3).
20. w = 0.0648 for the mirror image structure. The absolute configuration was also determined by measurement of the Bijvoet pairs.