A general approach to synthesis of labeled brassinosteroids: Preparation of [25,26,27-2h7]brassinolide with 60% isotopic purity from the parent brassinolide

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7525-7528

  Seto, Hideharu ^a   Fujioka, Shozo ^a   Koshino, Hiroyuki ^a   Yoshida, Shigeo ^a   Watanabe, Tsuyoshi ^b   Takatsuto, Suguru ^c  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b Tama Biochemical Co Ltd   (Japan)

^c JOETSU UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BRASSINOLIDE; DEUTERIUM; PHYTOHORMONE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEHYDRATION; HYDROXYLATION; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01636-0     Document Type: Article

References (17)

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5. 4. For examples see, Cohen, Z.; Keinan, E.; Mazur, Y.; Ulman, A. J. Org. Chem., 1976, 41, 2651-2652; Cohen, Z.; Mazur, Y. J. Org. Chem., 1979, 44, 2318-2320; Kiegiel, J.; Wovkulich, P. M.; Groves, J. T.; Neumann, R. J. Org. Chem. 1988, 53, 3891-3893; Uskokovic, M. R. Tetrahedron Lett. 1991, 32, 6057-6060.
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13. 2), 4.48 (1H, d, J=9.1 Hz, 23-H).
14. 10. This procedure was necessary to eliminate a side-reaction, C-5 epimerization, which was observed to a considerable extent when the conventional conditions for removal of the tetra-O-acetyl protecting groups of the BL congeners [5% methanolic potassium hydroxide, reflux: for an example, see ref. 8] were used.
15. +, 100), 486 (30).
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