First total synthesis of 4-methylthio-3-butenyl glucosinolate

Bioscience, Biotechnology and Biochemistry

Volumn 73, Issue 3, 2009, Pages 785-787

  Yamazoe, Sayumi ^a,b   Hasegawa, Koji ^a   Shigemori, Hideyuki ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

4 Methylthio 3 butenyl glucosinolate; Natural product; Phototropism; Radish; Synthesis

Indexed keywords

4-METHYLTHIO-3-BUTENYL GLUCOSINOLATE; NATURAL PRODUCT; PHOTOTROPISM; RADISH; SYNTHESIS;

ALDEHYDES; CHEMICAL REACTIONS; CHLORINE COMPOUNDS;

DERIVATIVES;

4 METHYLTHIO 3 BUTENYL GLUCOSINOLATE; 4-METHYLTHIO-3-BUTENYL GLUCOSINOLATE; GLUCOSINOLATE;

ARTICLE; CHEMISTRY; RADISH; STEREOISOMERISM; SYNTHESIS;

GLUCOSINOLATES; RAPHANUS; STEREOISOMERISM;

RAPHANUS SATIVUS;

EID: 65349183475     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80862     Document Type: Article

References (8)

1. Friis, P., and Kjaer, A., 4-Methylthio-3-butenyl isothiocyanate, the pungent principle of radish root. Acta Chem. Scand., 20, 698-705 (1966).
2. Hasegawa, T., Yamada, K., Kosemura, S., Yamamura, S., and Hasegewa, K., Phototropic stimulation induces the conversion of glucosinolate to phototropism-regulating substances of radish hypocotyls. Phytochemistry, 54, 275-279 (2000).
3. Papi, A., Orlandi, M., Bartolini, G., Barillari, J., Iori, R., Paolini, M., Ferroni, F., Fumo, M. G., Pedulli, G F., and Valgimigli, L., Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware daikon) sprouts. J. Agric. Food Chem., 56, 875-883 (2008).
4. Kosemura, S., Yamamura, S., and Hasegawa, K., Chemical studies on 4-methylthio-3-butenyl isothiocyanate from roots of Japanese radish (Raphanus sativus L.) in connection with raphanusanins, phototropism-regulating substances of radish hypocotyls. Tetrahedron Lett., 34, 481-484 (1993).
5. Davidson, N. E., Rutherford, T. J., and Botting, N. P., Synthesis, analysis and rearrangement of novel unnatural glucosinolates. Carbohydr. Res., 330, 295-307 (2001).
6. Lee, A. H. F., Chan, A. S. C, and Li, T., Synthesis of 5-(7-hydroxyhept-3-enyl)-l,2-dithiolan-3-one 1-oxide, a core functionality of antibiotic leinamycin. Tetrahedron, 59, 833-839 (2003).
7. Bonini, C, Checconi, M., Righi, G., and Rossi, L., Enantio and stereoselective synthesis of (5R,6S)-6-acetoxy-hexadecanolide, a mosquito oviposition attractant pheromone. Tetrahedron, 51, 4111-4116 (1995).
8. Wittig, G., and Schlosser, M., Über die herstellung von vinyläthern, vinylthioäthern und vinylhalogeniden auf der phosphylen-basis; IV. Mitteil. über phosphin-alkylene als olefinbildende reagenzien. Chem. Ber., 94, 1373-1383 (1961). 9) Visentin, M., Tava, A., Iori, R., and Palmieri, S., Isolation and identification for trans-4-(methylthio)-3-butenyl glucosinolate from radish roots (Raphanus sativus L.). J. Agric. Food Chem., 40, 1687-1691 (1992).