75258-86-5Relevant articles and documents
Studies in Antifertility Agents: Part XXV - 2-Carboxy-7-hydroxy-1-phenyl-1,2,3,4-tetrahydrofluorene
Tewari, S. C.,Rastogi, Shri Nivas,Anand, Nitya
, p. 139 - 142 (2007/10/02)
The synthesis and stereochemical assignments of 2-carboxy-7-hydroxy-1-phenyl-1,2,3,4-tetrahydrofluorene (17) are reported. 2-Arylidene-5-methoxy-1-indanones (5-8) have been prepared by condensation of 5-methoxy-1-indanone (1) with araldehydes (2-4).Addition of methyl acetoacetate onto 5 furnishes 2-carbomethoxy-7-methoxy-3-oxo-1-phenyl-1,2,3,9a-tetrahydrofluorene (9), which under acid hydrolysis gives the enone (10), and on treatment with ethanedithiol affords the thioketal (11).Desulphurization of 11 with Raney nickel yields 1,2-trans-2-carbomethoxy-7-methoxy-1-phenyl-1,2,3,4-tetrahydrofluorene (12).Catalytic hydrogenation of 12 affords possibly B/C-cis-1,2-trans-1,2,3,4,4a,9a-hexahydrofluorene (13).Alkaline hydrolysis of esters 11, 12 and 13 gives the corresponding acids 15, 16 and 14.Demethylation of 16 with BBr3-CH2Cl2 furnishes the title hydroxy acid (17).None of these compounds prevents pregnancy at a dose of 10 mg/kg in rats.