2515-12-0Relevant articles and documents
Synthesis of Symmetrical and Hybrid Dimeric Steroids by Double Suzuki-Miyaura Cross Coupling of 4-Bromo-3-oxo Steroids and Benzene-1,4-diboronic Acid
Flores-álamo, Marcos,Iglesias-Arteaga, Martín. A.,Mayorquín-Torres, Martha C.,Santiago-Sampedro, Gerardo I.
, p. 2909 - 2914 (2019/07/22)
Two symmetrical dimers and one hybrid dimer in which the steroid cores are connected by a 1,4-phenylene moiety were obtained by double Suzuki-Miyaura cross coupling of benzene-1,4-diboronic acid with 4-bromo-4-en-3-oxosteroids derived from cholesterol and diosgenin. Detailed NMR characterization of the obtained dimers is described.
Unambiguous assignment of 13C NMR signals in epimeric 4,5-epoxy-3-oxo-steroids assisted by X-ray diffraction and Gauge Invariant Atomic Orbitals calculation of absolute isotropic shieldings
Labra-Vazquez, Pablo,Galano, Annia,Romero-Avila, Margarita,Flores-Alamo, Marcos,Iglesias-Arteaga, Martin A.
, p. 107 - 125 (2013/09/12)
Complete assignments of the 13C signals of diastereomeric 4,5-epoxy-3-oxo steroids based on a combination of 1D and 2D NMR techniques are described The assignments were corroborated or corrected by calculation of the absolute isotropic 13C NMR shieldings using the Gauge Invariant Atomic Orbitals (GIAO) method at B3LYP/6-31+G(d,p) level. ARKAT-USA, Inc.
1,3-Chirality transfer by fragmentation of allylsulfinic acids: A diastereoselective approach to vinyl bromides related to trans-hydrindane or trans-decalin
Chochrek, Pawel,Wicha, Jerzy
, p. 2534 - 2542 (2008/03/12)
Diastereoselective approaches to vinyl bromides from bromoallylic alcohols by fragmentation of the respective allylsulfinic acids have been investigated. Bromoallylic alcohols 1a and 6 were transformed into the respective 1,3-benzothiazol-2-yl sulfides 2a and 7 by the Mitsunobu inversion reaction under modified conditions. The sulfides were then oxidized into sulfones 11a and 12a, respectively. Reduction of 11a and 12a with sodium borohydride gave the respective allylsulfinic acid salts 13a and 15 which, without isolation, were treated with aqeous tartaric acid. The salt 13a gave exclusively 5α-cholestane derivative 14a whereas 15 provided a mixture of the 5α and 5β derivatives 16 and 17 (after deprotection), the former prevailing. In an alternative approach, benzothiazolyl sulfides 2a and 7 were treated sequentially with BH3·THF and LiAlH4 to give thiols 18a and 19a, respectively. Oxidation of thiols 18a and 19a with oxaziridine 21 gave the respective sulfinic acids which, on gentle heating, afforded bromoolefins 14a and 22a, respectively, as the only products. Analogous reaction sequences starting from allylic alcohols devoid of the bromine substituent 1b and 8 have also been studied. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
