Synthesis of aromatic stigmastanes: application to the synthesis of aromatic analogs of brassinosteroids

In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic ana...

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Bibliographic Details
Published in:Tetrahedron 2012-05, Vol.68 (19), p.3685-3691
Main Authors: Acebedo, Sofía L., Alonso, Fernando, Ramírez, Javier A., Galagovsky, Lydia R.
Format: Article
Language:English
Subjects:
A-ring
Alicyclic compounds, terpenoids, prostaglandins, steroids
Analogs
Aromatic stigmastanes
Bioactivity
Biochemistry
Brasses
Brassinosteroids
Chemistry
Exact sciences and technology
Hormones
Organic chemistry
Preparations and properties
Steroids
Synthesis (chemistry)
Tasks
Tetrahedrons
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Summary:In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic analogs showed a reduced but significant bioactivity when compared to the natural hormones. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.03.082