caa a22 4500 605528535 CHVBK 20210128100813.0 cr unu---uuuuu 210128e20150101xx s 000 0 eng 10.1134/S1070428015010133 doi (NATIONALLICENCE)springer-10.1134/S1070428015010133 Synthesis of 14α-substituted androstanes—Key compounds in the synthesis of 14-substituted brassinosteroids [Elektronische Daten] [A. Baranovskii, D. Bolibrukh, B. Schneider] Ethyl 3-(6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-17-oxo-5α-androstan-14α-yl)propanoate, the key intermediate product in the synthesis of brassinosteroids modified in the D ring, was synthesized from 6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-androsta-14,16-dien-17-yl acetate via reaction sequence including Diels-Alder cycloaddition with phenyl vinyl sulfone, dihydroxylation, Malaprade diol cleavage, and selective Horner-Wadsworth-Emmons olefination. Pleiades Publishing, Ltd., 2015 Baranovskii A. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Bolibrukh D. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut Schneider B. Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knöll Str. 8, D-07745, Jena, Germany aut Russian Journal of Organic Chemistry Pleiades Publishing 51/1(2015-01-01), 78-85 1070-4280 51:1<78 2015 51 11178 https://doi.org/10.1134/S1070428015010133 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015010133 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Baranovskii A. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 700 1- Bolibrukh D. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus aut NATIONALLICENCE 700 1- Schneider B. Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knöll Str. 8, D-07745, Jena, Germany aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/1(2015-01-01), 78-85 1070-4280 51:1<78 2015 51 11178