Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

• Published in: Russian journal of bioorganic chemistry Vol. 36; no. 6; pp. 746 - 754
• Main Authors: Khripach, V. A, Zhabinskii, V. N, Gulyakevich, O. V, Konstantinova, O. V, Misharin, A. Yu, Mekhtiev, A. R, Timofeev, V. P, Tkachev, Ya. V
• Format: Journal Article
• Language: English
• Published: Dordrecht Dordrecht : SP MAIK Nauka/Interperiodica 01-11-2010; SP MAIK Nauka/Interperiodica
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; brassinolide; brassinosteroids; Life Sciences; olefination; Organic Chemistry; secasterol; sulfones; brassinolide; brassinosteroids; sulfones; secasterol; olefination
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162010060117

The convergent synthesis of biosynthetic precursors of brassinosteroids with a Δ₂-bond in cycle A—secasterol and 24-episecasterol—was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Δ₂₂-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.