The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation |
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| Authors: | Khripach Vladimir A Zhabinskii Vladimir N Fando Galina P Kuchto Alla I Lyakhov Alexander S Govorova Alla A Groen Marinus B van der Louw Jaap de Groot Aede |
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| Institution: | Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str., 5/2, 220141 Minsk. khripach@iboch.bas-net.by |
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| Abstract: | A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate delta13(17)-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)-triene was determined by X-ray analysis. |
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| Keywords: | Grob fragmentation X-ray analysis Secosteroids Nine membered ring |
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