Synthesis of 2-Deoxybrassinosteroids Analogs with 24-nor, 22(S )-23-Dihydroxy-Type Side Chains from Hyodeoxycholic Acid

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Rodrigo CarvajalLuis Espinoza

Abstract

Natural brassinosteroids are widespread in the plant kingdom and it is known that they play an important role in regulating plant growth. In this study, two new brassinosteroid analogs with shorter side chains but keeping the diol function were synthesized. Thus, the synthesis of 2-deoxybrassinosteroids analogs of the 3α-hydroxy-24-nor, 22,23-dihydroxy-5α-cholestane side chain type is described. The starting material is a derivative from hyodeoxycholic acid (4), which was obtained with an overall yield of 59% following a previously reported five step route. The side chain of this intermediate was modified by oxidative decarboxylation to get a terminal olefin at the C22-C23 position (compound 20) and subsequent dihydroxylation of the olefin. The resulting epimeric mixture of 21a, 21b was separated and the absolute configuration at the C22 carbon for the main product 21a was elucidated by single crystal X-ray diffraction analysis of the benzoylated derivative 22. Finally, lactonization of 21a through a Baeyer-Villiger oxidation of triacetylated derivative 23, using CF₃CO₃H/CHCl₃ as oxidant system, leads to lactones 24 and 25 in 35% and 14% yields, respectively. Deacetylation of these compounds leads to 2-deoxybrassinosteroids 18 ...Continue Reading

References

Jan 1, 1975·Journal of the Chemical Society. Perkin Transactions 1·M IshiguroM Okubayashi
Oct 1, 1968·Tetrahedron Letters·A S VaidyaA S Rao
Feb 22, 2002·Steroids·Martín A Iglesias-ArteagaFrancisco Coll Manchado
Feb 1, 2008·Journal of Applied Crystallography·Rob W W HooftAnthony L Spek
May 31, 2013·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Simon ParsonsTrixie Wagner
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·Luc J BourhisHorst Puschmann
Sep 14, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Heidy HerreraLuis Espinoza

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Citations

Dec 22, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jocelyn OyarceLuis Espinoza Catalán
Mar 12, 2020·International Journal of Molecular Sciences·Katy DíazYamilet Coll
Jan 16, 2021·International Journal of Molecular Sciences·Juan Pablo Figueroa-MacíasLuis Espinoza
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Karoll FerrerLuis Espinoza

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Methods Mentioned

BETA
X-ray
NMR
acetylation

Software Mentioned

APEX2
SHELXL )
solve
olex2

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