21610-87-7Relevant academic research and scientific papers
Sequential pericyclic reaction of ene-diallene: synthesis of (±)-estrone
Hakuba, Hirohumi,Kitagaki, Shinji,Mukai, Chisato
, p. 12639 - 12645 (2007)
The one-pot construction of perhydrophenanthrene from an acyclic substrate was achieved via a sequential pericyclic reaction, which involved the in situ generation of ene-diallene species due to Myers' propargyl alcohol-allene transformation. The resulting perhydrophenanthrene derivative could be successfully converted into (±)-estrone.
Efficient regioselective a-ring functionalization of oestrogens
Bulman Page, Philip C.,Hussain, Fazal,Maggs Paul Morgan, James L.,Kevin Park
, p. 2059 - 2068 (2007/10/02)
Complete series of 2-halo- and 2-cyano-oestrogens have been prepared in good to high yields: 2-chloro, 2-bromo, 2-iodo, and 2-cyano derivatives via oestrogen-thallium (III) bis(trifluoroacetate) intermediates, and 2- and 4- fluorooestrogens by direct functionalization using N-fluoropyridinium triflate.
Applications of 1-Alkoxycarbonyl- and 1-Acyl-v-triazolopyridines as Acylating Reagents
Torrini, Ines,Zecchini, Giampiero Pagani,Agrosi, Francesco,Paradisi, Mario Paglialunga
, p. 1459 - 1463 (2007/10/02)
Selective N-protection of hydroxyamino esters has been readily achieved using 1-alkoxycarbonyl- or 1-acyl-v-triazolopyridines.The amide-type triazolides reacted with alcohols in the presence of DBU at room temperature to afford in high yields the corresponding esters.The different reactivity of 1- and 3-alkoxycarbonyl derivatives of the title bicyclic system toward primary amines has been further investigated.
PREPARATION OF 16-SUBSTITUTED 3-HYDROXYESTRA-1,3,5(10)-TRIENE-17-ONE STARTING WITH THE BROMINATION OF ESTRONE ACETATE
Fedorova, O. I.,Morozova, L. S.,Alekseeva, L. M.,Grinenko, G. S.
, p. 437 - 440 (2007/10/02)
The bromination of estrone acetate (Ia) leads to a mixture of acetates of 16α-bromo-16β-bromo-, and 16,16-dibromoestrone (IIa, IIIa, and IVa) in a ratio of 63:28:9.On treatment with an aqueous methanolic solution of potash, depending on the conditions, a mixture of (IIa) and (IIIa) gives 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one (V) or 3,17β-dihydroxyestra-1,3,5(10)-trien-16-one (VI).When 5 g of (Ia) was brominated with 2.8 g of Br2 in chloroform and the products were chromatographed on silica gel, 0.36 g of (IVa), C20H22Br2O3, mp 165-166 deg C (from ether) 0.37 g of (IIIa), mp 169-170.5 deg C, 4.6 g of a mixture of (IIa) and (IIIa), 30 mg of (Ia) and 0.2 g of a mixture of 16α- and 16β-bromoestrones was obtained.The action of potash on a mixture of (IIa) and (IIIa) in aqueous MeOH at 20 deg C led to the epimerization of the (IIa) into (IIIa) and then the conversion of the latter into (V) with mp 203.5-206 deg C; diacetate with mp 172-173 deg C (acetone-ethanol).Similarly, but with heating (98 deg C, 3 h), a mixture of (IIa) and (IIIa) was converted into (VI), with mp 234-236 deg C.Characteristics of the IR and PMR spectra of the compounds obtained are given.
