TY - JOUR
T1 - Synthesis of thiophene-containing steroid-like molecules via olefinic cyclization reactions
AU - Corvers, A.
AU - van Mil, J.H.
AU - Scheffers - Sap, Miek
AU - Buck, H.M.
PY - 1977
Y1 - 1977
N2 - Ring closure of 2-methyl-5-(2-thienyl)-2-pentene (4a) and 2-methyl-5-(3-thienyl)-2-pentene (4b) to the corresponding 4,5,6,7-tetrahydrobenzo[b]thiophenes 5a respectively 5b, is described. In order to establish the possibility of the direct synthesis of steroids in which the A-ring is replaced by thiophene, 2-[6-(2-thienyl)-(Z)-3-hexenyl]-3-methyl-2-cyclopenten-1-ol (9a) and its (3-thienyl)-substituted analogue (Z)- and (E)-isomers 9b and 9c respectively, were prepared. The (Z)-isomers failed to give tetracyclic compounds in contrast to 9c which furnished compound 14 in moderate yield.
AB - Ring closure of 2-methyl-5-(2-thienyl)-2-pentene (4a) and 2-methyl-5-(3-thienyl)-2-pentene (4b) to the corresponding 4,5,6,7-tetrahydrobenzo[b]thiophenes 5a respectively 5b, is described. In order to establish the possibility of the direct synthesis of steroids in which the A-ring is replaced by thiophene, 2-[6-(2-thienyl)-(Z)-3-hexenyl]-3-methyl-2-cyclopenten-1-ol (9a) and its (3-thienyl)-substituted analogue (Z)- and (E)-isomers 9b and 9c respectively, were prepared. The (Z)-isomers failed to give tetracyclic compounds in contrast to 9c which furnished compound 14 in moderate yield.
U2 - 10.1002/recl.19770960106
DO - 10.1002/recl.19770960106
M3 - Article
SN - 0165-0513
VL - 96
SP - 18
EP - 22
JO - Recueil des Travaux Chimiques des Pays-Bas
JF - Recueil des Travaux Chimiques des Pays-Bas
IS - 1
ER -