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Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone

Natalya Anatol'evna Veskina 1
Natalya Anatol'evna Veskina
, 
Aliya Shamilevna Ibragimova 1
Aliya Shamilevna Ibragimova
, 
Ilgiz V Galyautdinov 1
Ilgiz V Galyautdinov
, 
Leonard Mukhibovich Khalilov 1
Leonard Mukhibovich Khalilov
, 
Viktor Nikolaevich Odinokov 1
Viktor Nikolaevich Odinokov
10.1016/j.mencom.2010.09.019
Published 2010-09-09
Communication , Volume 20, Issue 5, 293-295
7
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Veskina N. A. et al. Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone // Mendeleev Communications. 2010. Vol. 20. No. 5. pp. 293-295.
GOST all authors (up to 50) Copy
Veskina N. A., Ibragimova A. S., Galyautdinov I. V., Khalilov L. M., Odinokov V. N. Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone // Mendeleev Communications. 2010. Vol. 20. No. 5. pp. 293-295.
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TY - JOUR
DO - 10.1016/j.mencom.2010.09.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.019
TI - Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone
T2 - Mendeleev Communications
AU - Veskina, Natalya Anatol'evna
AU - Ibragimova, Aliya Shamilevna
AU - Galyautdinov, Ilgiz V
AU - Khalilov, Leonard Mukhibovich
AU - Odinokov, Viktor Nikolaevich
PY - 2010
DA - 2010/09/09
PB - Mendeleev Communications
SP - 293-295
IS - 5
VL - 20
ER -
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@article{2010_Veskina,
author = {Natalya Anatol'evna Veskina and Aliya Shamilevna Ibragimova and Ilgiz V Galyautdinov and Leonard Mukhibovich Khalilov and Viktor Nikolaevich Odinokov},
title = {Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone},
journal = {Mendeleev Communications},
year = {2010},
volume = {20},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.019},
number = {5},
pages = {293--295},
doi = {10.1016/j.mencom.2010.09.019}
}
MLA
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Veskina, Natalya Anatol'evna, et al. “Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone.” Mendeleev Communications, vol. 20, no. 5, Sep. 2010, pp. 293-295. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.09.019.

Keywords

25-hydroxydachryhainansterone
ecdysteroids
oxetane cycle, 7,9-dien systeme

Abstract

9α,14α-Epoxy-14-deoxy-20-hydroxyecdysone diacetonide on treatment with NaBH4 undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by β→α epimerization of the adjacent HC5 centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing β-HC5 configuration due to the re-epimerisation at this centre.

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