A short convergent synthesis of the side chains of brassinolide,cathasterone, and cryptolide |
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Authors: | Alaksiej Hurski Vladimir Zhabinskii Vladimir Khripach |
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Affiliation: | Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5/2, 220141 Minsk, Belarus |
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Abstract: | A new approach to steroidal derivatives of the campestane series, containing the 22α-hydroxy-, 22α,23α-dihydroxy-, and 22α-hydroxy-23-ketone moieties characteristic of brassinolide and its congeners, has been developed. The key step is the coupling of a steroidal C-22 aldehyde with an anion derived from a specially synthesized thioacetal-containing chiral synthon. The cathasterone and cryptolide side chains are prepared by reductive or hydrolytic thioketal removal, respectively. The brassinolide side chain is obtained by DIBAL-H reduction of the TBS-protected 22α-hydroxy-23-ketone. |
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