Synthesis of hexadeuterated 23-dehydroxybrassinosteroids

Steroids

Volumn 67, Issue 13-14, 2002, Pages 1101-1108

  Khripach, Vladimir A ^a   Zhabinskii, Vladimir N ^a   Antonchick, Andrey P ^a   Konstantinova, Olga V ^a   Schneider, Bernd ^b  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Brassinolide; Brassinosteroids; Labeled compounds; Plant growth hormone

Indexed keywords

23 DEHYDROXYBRASSINOSTEROID; 3 HYDROXY 2 METHYLPROPIONIC ACID; ALDEHYDE DERIVATIVE; BRASSINOLIDE; DEUTERIUM; HYDROXYL GROUP; IODINE DERIVATIVE; KETONE; STEROID; SULFONE; UNCLASSIFIED DRUG; HETEROCYCLIC STEROID;

ALKYLATION; ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; NONHUMAN; PHYTOCHEMISTRY; REDUCTION; STEREOCHEMISTRY; STEROID ANALYSIS; STEROIDOGENESIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DEUTERIUM; MOLECULAR STRUCTURE; STEROIDS, HETEROCYCLIC;

EID: 0036889657     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(02)00071-5     Document Type: Article

References (28)

1. Khripach VA, Zhabinski VN, de Groot AE. Brassinosteroids: a new class of plant hormones. San Diego: Academic Press, 1999.
2. Sakurai A, Yokota T, Clouse SD, editors. Brassinosteroids: steroidal plant hormones. Tokyo: Springer, 1999.
3. Fujioka S., Inoue T., Takatsuto S., Yanagisawa T., Yokota T., Sakurai A. Identification of a new brassinosteroid, cathasterone, in cultured cells of Catharanthus roseus as a biosynthetic precursor of teasterone. Biosci. Biotech. Biochem. 59:1995;1543-1547.
4. Szekeres M., Németh K., Koncz-Kálman Z., Mathur J., Kauschmann A., Altmann T.et al. Brassinosteroids rescue the deficiency of CYP90, a cytochrome P450, controlling cell elongation and de-etiolation in Arabidopsis. Cell. 85:1996;171-182.
5. 6 oxidation. Phytochemistry. 44:1997;609-613.
6. Fujioka S., Noguchi T., Yokota T., Takatsuto S., Yoshida S. Brassinosteroids in Arabidopsis thaliana. Phytochemistry. 48:1998;595-599.
7. Takatsuto S, Yokota T. Biochemical analysis of natural brassinosteroids. In: Sakurai A, Yokota T, Clouse SD, editors. Brassinosteroids: steroidal plant hormones. Tokyo: Springer, 1999. p. 47-68.
8. Ihara Chem. Ind., Ltd., Japan, assignee. (22S)-B-Homo-7-oxa-5α-cholestan-6-one-3β,22-diol. Japan Kokai Tokkyo Koho JP 59 27,886 [84 27,886], 1982 [C.A. 101, 130976].
9. Voigt B., Bruhn C., Wagner C., Merzweiler K., Adam G. Synthesis of 24-epicathasterone and related new brassinosteroids. Proc. Plant Growth Regul. Soc. Am. 24:1997;138-139.
10. Voigt B., Porzel A., Bruhn C., Wagner C., Merzweiler K., Adam G. Synthesis of 24-epicathasterone and related brassinosteroids with modified side chain. Tetrahedron. 53:1997;17039-17054.
11. Jin F, Xu Y, Huang W. 2,2-Difluoro enol silyl ethers: convenient preparation and application to the synthesis of novel fluorinated brassinosteroids. J Chem Soc, Perkin Trans I 1993:795-9.
12. Takatsuto S, Kuriyama H, Noguchi T, Suganuma H, Fujioka S, Sakurai A. Synthesis of cathasterone and its related putative intermediates in brassinolide biosynthesis. J Chem Res Synopsis 1997:418-9.
13. Takatsuto S, Watanabe T, Gotoh C, Kuriyama H, Noguchi T, Fujioka S. A convenient synthesis of (22S)-22-hydroxycampesterol and some related steroids. J Chem Res Synopsis 1998:176-7.
14. Werner F., Parmentier G., Luu B., Dinan L. A convenient stereoselective synthesis of castasterone and its analogs using arsenic ylides. Tetrahedron. 52:1996;5525-5532.
15. Nagano H, Matsuda M, Yajima T. Stereoselective synthesis of 24-alkyl-22-hydroxy sterols based on chelation-controlled radical reactions. J Chem Soc, Perkin Trans I 2001:174-82.
16. 6 )cholesterol and derivatives substituted in the side chain. J Chem Soc, Perkin Trans I 1983:2563-7.
17. Holm T., Crossland I. A simple preparation of hexadeuteriocholesterol. J. Labelled Compd. Radiopharm. 38:1996;803-808.
18. Piatak D.M., Wicha J. Various approaches to the construction of aliphatic side chains of steroids and related compounds. Chem. Rev. 78:1978;199-241.
19. Zhabinskii V.N., Olkhovick V.K., Khripach V.A. Methods of stereoselective construction of steroidal side chains. Zhurn. Org. Khim. 32:1996;327-363.
20. Schmittberger T., Uguen D. A formal synthesis of brassinolide. Tetrahedron Lett. 38:1997;2837-2840.
21. Mori K., Sakakibara M., Ichikawa Y., Ueda H., Okada K., Umemura T.et al. Synthesis of (22S,23S)-homobrassinolide and brassinolide from stigmasterol. Tetrahedron. 38:1982;2099-2109.
22. Tachibana Y, Yokoyama S, Tejima T. Inventors. Nisshin Flour Milling Co., assignee. Preparation of phenyl sulfones as intermediates for brassinolide or Vitamin D. Japan Kokai Tokyo Koho JP 05,221,955 [93,221,955], 1992 [C.A. 120, 106537].
23. Okada K., Mori K. Synthesis of brassinolide analogs and their plant growth-promoting activity. Agric. Biol. Chem. 47:1983;89-95.
24. Khripach VA, Zhabinskii VN, Olkhovick VK, Akhrem AA. Synthesis of 28-nor analogs of brassinolide. Vesti AN BSSR Ser Khim Navuk 1990:69-74.
25. 3: 24,24-dihomo-25-hydroxycholecalciferol and (22E)-22-dehydro-24,24-dihomo-25-hydroxycholecalciferol. Bioorg. Chem. 21:1993;13-23.
26. House H.O., Larson J.K. The use of β-keto sulfones as synthetic intermediates. J. Org. Chem. 33:1968;61-65.
27. Rossi S, Pagani G. 3-Phenyl-2H-thiopyran-1,1-dioxide and 2H-thiochromen-1,1-dioxide. Synthesis and acidic properties. Tetrahedron Lett 1966:2129-34.
28. 3 ]brassinosteroids Steroids. 67:2002;587-595.