81644-34-0Relevant academic research and scientific papers
Synthetic Modifications of Withanolides with an α-Orientated Side-Chain
Glotter, Erwin,Kumar, Sandeep,Sahai, Mahendra,Goldman, Alex,Kirson, Isaac,Mendelovici, Marioara
, p. 739 - 745 (2007/10/02)
In view of the antitumour activity of withanolide E and 4β-hydroxywithanolide E, synthetically modified analogues were prepared.In these compounds, the α-orientation of the side-chain was retained.Its degree of bending with respect to the carbocyclic skeleton depends on the presence or absence of the 14α-OH group.Elimination of this group leads to the formation of the 14,20-oxido-bridged and Δ14-compounds.Epoxidation of the latter afforded 14α,15α-epoxides.With the exception of several 5,6-chlorohydrins, most compounds possess an epoxide ring, allylic or homoallylic with respect to the ring A enone.
Studies on the 5β,6β-Epoxide Opening in Withanolides
Nittala, S. Sarma,Lavie, David
, p. 2835 - 2840 (2007/10/02)
The opening of the steroidal 5β,6β-epoxide group, with or without an adjacent 4β-hydroxy-group, was investigated under thermal conditions on a solid support, and in the presence of sodium chloride for several withanolides.The study was expanded with the compound being treated with sulphuric acid in acetone at various concentrations and temperatures.Different reaction products (diaxial, diequatorial, or rearranged) were obtained depending on the conditions and the presence or absence of a 2,3-double bond in ring A of these 1-keto-steroids.
