Synthesis of new 10 beta-propargylic and 11 beta-allenic steroidal spirolactones.
As part of continuing studies on the synthesis of new, biologically interesting 11 beta-substituted steroidal spirolactones, we describe here the competition between 10 beta-propargylation and 11 beta-allenylation. Grignard addition of allenyl magnesium bromide to an appropriate 5,10-epoxy-9(11)-olefin provides 10 beta-propargylation or 11 beta-allenylation. The role of the catalytic effect of copper chloride and of the solvent is evaluated. Confirmation of the structural assignments of these new 3,3-ethylenethioxy-10 beta-propargyl (or 11 beta-allenyl)-19-nor-17 alpha-pregna-4,9-diene-21,17-carbolactones is reported.
Faraj
H
H
INSERM U 300, Faculté de Pharmacie, Montpellier, France.
Aumelas
A
A
Claire
M
M
Rondot
A
A
Auzou
G
G
D015394:Molecular Structure; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013256:Steroids / Q000138:chemical synthesis*
D013256:Steroids; D013148:Spironolactone