Synthesis of 14α-substituted androstanes—Key compounds in the synthesis of 14-substituted brassinosteroids

Verfasser / Beitragende:
[A. Baranovskii, D. Bolibrukh, B. Schneider]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/1(2015-01-01), 78-85
Format:
Artikel (online)
ID: 605528535
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024 7 0 |a 10.1134/S1070428015010133  |2 doi 
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245 0 0 |a Synthesis of 14α-substituted androstanes—Key compounds in the synthesis of 14-substituted brassinosteroids  |h [Elektronische Daten]  |c [A. Baranovskii, D. Bolibrukh, B. Schneider] 
520 3 |a 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. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Baranovskii  |D A.  |u Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus  |4 aut 
700 1 |a Bolibrukh  |D D.  |u Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus  |4 aut 
700 1 |a Schneider  |D B.  |u Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knöll Str. 8, D-07745, Jena, Germany  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/1(2015-01-01), 78-85  |x 1070-4280  |q 51:1<78  |1 2015  |2 51  |o 11178 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Baranovskii  |D A.  |u Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Bolibrukh  |D D.  |u Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Schneider  |D B.  |u Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knöll Str. 8, D-07745, Jena, Germany  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/1(2015-01-01), 78-85  |x 1070-4280  |q 51:1<78  |1 2015  |2 51  |o 11178