25819-77-6Relevant academic research and scientific papers
Synthesis and Configurational Assignment of Epimeric 22-Hydroxy-, 23,24-Acetylenic, Olefinic or Epoxy Steroids Using Carbon-13 NMR Spectroscopy
Hazra, Braja G.,Pore, Vandana S.,Joshi, Padmakar L.,Padalkar, Sharmila N.,Deshpande, Shubhada A.,Rajamohanan, Pattuparambil R.
, p. 605 - 608 (1993)
Stereoisomers of steroidal 22-hydroxy-, 23-acetylenic, 23-olefinic and 23,24-isomeric epoxides were synthesized from C-22 aldehydes and their (13)C NMR spectra were analysed.A correlation regarding the combined effect of the 22-hydroxy and 23,24-substituents on the stereochemistry of the attached groups at C-22, -23 and -24 is derived.KEY WORDS: Brassinolide; Configurational assignment; 22-Hydroxy-23,24-epoxysteroids; (13)C NMR
Stereocontrolled synthesis of dafachronic acid A, the ligand for the DAF-12 nuclear receptor of Caenorhabditis elegans
Giroux, Simon,Corey
, p. 9866 - 9867 (2007)
An efficient synthetic route to the DAF-12 nuclear receptor ligand of C. elegans, dafachronic acid, is described that starts with the abundant plant sterol β-stigmasterol and proceeds in 37% overall yield. The synthesis establishes the structure of this r
Synthesis and bioactivities of steroid derivatives as antifungal agents
Chung, Sung-Kee,Ryoo, Chung Hwan,Yang, Hong Woon,Shim, Jeung-Yeop,Kang, Myung Goo,Lee, Ki Wha,King, Heui Il
, p. 15899 - 15914 (1998)
A series of lanosterol and cholesterol derivatives with modified side chain structures, which might interfere with sterol C24-methyltransferase in the ergosterol biosynthesis as substrate analogs, have been synthesized. The in vitro bioassay studies have shown that some of these compounds, in particular with C24-amino- and thio-functionalities, possess potent antifungal activities. in vivo. Bioassays have also been carried out for the leading compounds.
Probing the mechanism of action of amphotericin B
James, Phillip R.,Rawlings, Bernard J.
, p. 505 - 508 (1996)
Transmembrane spanning dimers of cholesterol were unable to form ion channels with amphotericin B: We suggest that the two 'half pores' as proposed by De Kruijff may be aligned unsymmetrically.
Synthesis of a Cholesterol Side-Chain Triazole Analogue via 'Click' Chemistry
Seck, Insa,Fall, Alioune,Lago, Carmen,Sène, Massène,Gaye, Mohamed,Seck, Matar,Gómez, Generosa,Fall, Yagamare
, p. 2826 - 2830 (2015)
An efficient preparation of a cholesterol analogue possessing a triazole ring is achieved starting from commercially available stigmasterol. The procedure is based on a [3+2] cycloaddition of a cholesterol possessing a side-chain terminal azide with a ter
Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction
Rosenbaum, Nicolai,Schmidt, Lisa,Mohr, Florian,Fuhr, Olaf,Nieger, Martin,Br?se, Stefan
supporting information, p. 1568 - 1574 (2021/02/26)
In this study, we report a convenient and high yielding formal semisynthesis of demethylgorgosterol, a marine steroid with an intriguing sidechain containing a cyclopropane unit. This was achieved through the synthesis of an advanced ketone intermediate.
Synthesis of 28-homobrassinosteroids modified in the 26-position
Litvinovskaya,Raiman,Khripach
experimental part, p. 647 - 652 (2010/07/08)
28-Homobrassinosteroids modified in the 26-position were synthesized from 22-hydroxy-23-ensteroids using Claisen rearrangement and subsequent cis-hydroxylation of the resulting Δ22-derivative.
Synthesis of [26,27-2H6]brassinosteroids from 23,24-bisnorcholenic acid methyl ester
Antonchick, Andrey P.,Schneider, Bernd,Zhabinskii, Vladimir N.,Khripach, Vladimir A.
, p. 617 - 628 (2007/10/03)
A number of hexadeuterated brassinosteroids (BS) containing a hydroxy group at C-22 or a 22R,23R-diol function were prepared starting from 23,24-bisnorcholenic acid methyl ester for biosynthetic studies. Synthesis of the cyclic part was accomplished via t
Stereoselective Synthesis of Squalamine Dessulfate
Moriarty, Robert M.,Enache, Livia A.,Kinney, William A.,Allen, Craig S.,Canary, James W.,et al.
, p. 5139 - 5142 (2007/10/02)
Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol.The key step is establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-met
Stereoselective synthesis of (22R,23R,24S)-3β-Hydroxy-5-ene-22,23-dihydroxy-24-methyl-cholestane: A Brassinolide Intermediate from 16-Dehydropregnenolone Acetate
Hazra, Braja G.,Joshi, Padmakar L.,Bahule, Bharat B.,Argade, Narshinha P.,Pore, Vandana S.,Chordia, Mahendra D.
, p. 2523 - 2532 (2007/10/02)
A new synthesis of the important aldehyde 1 from easily available 16-Dehydropregnenolone acetate (16-DPA) in high yield is described.The aldehyde 1 is converted to triol 24, involving a stereoselective generation of all the four chiral centers in the brassinolide side chain.The important features of this synthesis is stereospecific generation of the acetate 14 through ene reaction using three different catalysts as well as regioselective wittig reaction on the acetoxy aldehyde 20.Conversion of triol 24 to brassinolide is known, hence this constitutes a formal total synthesis of brassinolide.
