ISSN:
1573-9171
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 1. The condensation of 1,2,3,4-tetrahydro-1-vinyl-1,6-naphthalenediol (II) with 2-methyl-1,3-cyclohexanedione gives 3-hydroxy-8-14-seco-D-homoestra-1,3,5(10),9(11)-tetraene-14,17a-dione (V), which under the conditions of the reaction is cyclized into 3,14-dihydroxy-8Β-d-homoestra-1,3,5(10),9(11)-tetraen-17a-one (VI) and at higher temperature also into didehydro-d-homoestrone (I), which can thus be prepared from 3,4-dihydro-6-hydroxy-l(2H)-naphthalenone (III) in two stages with an over-all yield of above 50%. 2. The analogous condensation of the diol (II) with 2-methyl-1,3-cyclopentanedione gives 3,14-dihydroxyestra-1,3,5(10),8(9)-tetraen-17-one (VIII), which is readily dehydrated to didehydroestrone (IX) in an over-all yield of about 20%.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00850157
Permalink