- THE OXIDATION OF A STEROIDAL BROMOHYDRIN REVISITED
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A comparative study was made of the reactions of 5-bromo-3β,6β-dihydroxy-5α-androstan-17-one 3-acetate (1) with lead tetraacetate alone and in the presence of iodine in both high intensity visible light and in total darkness using a variety of solvents.Markedly different product profiles were obtained under the different reaction conditions, making our results of both practical importance and theoretical interest.
- Jennings, Bojan Hamlin,Yelle, Lauren Marie
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- Ultrasound assisted remote functionalization of non-activated carbon atoms: Efficient in situ formation of tetrahydrofurans by sonolysis of bromohydrins with (diacetoxyiodo)benzene/I2
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Ultrasonic irradiation of bromohydrins in the presence of (diacetoxyiodo)benzene and I2 generates alkoxyl radicals which lead in situ to intramolecular hydrogen abstraction on the C-19 non-activated carbon atoms in steroids producing tetrahydrofurans selectively in very good yields. Photolysis was less effective in promoting such conversions.
- Costa, Saul C. P.,Moreno, M. J. S. Miranda,Saì? e Melo, M. Luisa,Campos Neves, Andreì? S.
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- Synthetic study of strongylophorines: stereoselective construction of the characteristic lactone bridge
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Herein, we report an efficient construction of the lactone bridge of strongylophorine-2, which is a meroditerpenoid isolated from Strongylophora durissima and an inhibitor for HIF-1 transcriptional pathway. Starting from dehydroepiandrosterone acetate, the characteristic lactone has been constructed in 5.4% over 18 steps by employing, (1) modified oxy radical-mediated C–H functionalization at the C24 methyl group, and (2) four-step manipulation of C4 quaternary carbon stereogenic center. The lactone synthesized here is expected as a precursor for (8-desmethyl)strongylophorine-2 which is of particular interest in terms of structure–activity relationships in the inhibition of HIF-1 transcriptional pathway.
- Oikawa, Yuya,Uchiyama, Daiki,Shirasawa, Takuya,Oikawa, Masato,Ishikawa, Yuichi
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supporting information
p. 3949 - 3951
(2016/08/09)
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- COMPOUNDS AND METHODS FOR TREATING NEOPLASIA
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The invention features compounds, pharmaceutical compositions and methods useful for the treatment of neoplasia. In particular embodiments, the compounds of the invention are useful for the treatment of multidrug resistant neoplasia.
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Page/Page column 94
(2012/02/13)
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- 19-Oxygenated-5α-androstanes for the enhancement of libido
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Derivatives of 19-oxygenated-5α-androstanes are described which are useful in enhancing the libido and related psychic attitudes in mammals.
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