Synthesis of 22- and 23-dehydroxybrassinosteroids of the stigmastane series-Reference-Cited by-同舟云学术

Synthesis of 22- and 23-dehydroxybrassinosteroids of the stigmastane series

Published:2023-09-04 Issue:3 Volume:59 Page:202-210
ISSN:2524-2342
Container-title:Proceedings of the National Academy of Sciences of Belarus, Chemical Series
language:
Short-container-title:Vescì Akademìì navuk Belarusì. Seryâ himičnyh navuk

Author:

Khripach V. A.¹,Zhabinskii V. N.¹,Sikorov E. V.¹,Lazarev S. I.¹

Affiliation:

1. Institute of Bioorganic Chemistry of the National Academy of Sciences of Belarus

Abstract

The synthesis of previously undescribed 22- and 23-deoxyanalogues of homocastasterone has been carried out, which makes it possible to obtain target compounds without replacing the carbon skeleton of the side chain. The key reactions in their synthesis were epoxy ring opening and radical debromination.

Publisher

Publishing House Belorusskaya Nauka

Subject

Inorganic Chemistry,Organic Chemistry,Chemistry (miscellaneous),Analytical Chemistry

Reference18 articles.

1. Khripach V. A., Zhabinskii V. N., Groot A. E. de. Brassinosteroids. A New Class of Plant Hormones. San Diego, Academic Press, 1999. 456 p. https://doi.org/10.1016/B978-0-12-406360-0.X5000-X

2. Bajguz A., Hayat S., Ahmad A. Brassinosteroids – Occurence and Chemical Structures in Plants. Brassinosteroids: A Class of Plant Hormone. Dordrecht, Springer, 2011, pp. 1–27. https://doi.org/10.1007/978-94-007-0189-2_1

3. Wei Z., Li J. Regulation of brassinosteroid homeostasis in higher plants. Frontiers in Plant Science, 2020, vol. 11, pp. 583622. https://doi.org/10.3389/fpls.2020.583622

4. Choe S. W., Dilkes B. P., Fujioka S., Takatsuto S., Sakurai A., Feldmann K. A. The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22a-hydroxylation steps in brassinosteroid biosynthesis. Plant Cell, 1998, vol. 10, no. 2, pp. 231–243. https://doi.org/10.1105/tpc.10.2.231

5. Fujita S., Ohnishi T., Watanabe B., Yokota T., Takatsuto S., Fujioka S., Yoshida S., Sakata K., Masaharu M. Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols. Plant Journal, 2006, vol. 45, no. 5, pp. 765–774. https://doi.org/10.1111/j.1365-313X.2005.02639.x