A novel route to 3-hydroxy-16,17-seco-estrone derivatives (NOTE)

Starting from 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (1b), 17-tosylate 2b and also 17-chloro-, 17-bromo- and 17-iodo-derivatives 4b, 5b, and 6b, were obtained. The fluoro-derivative 3b was obtained from 2b in the reaction with tetrabutyl ammonium fluoride. The deprotection of the 3-hydroxyl group was achieved by action of hydrogen in presence of Pd/C as a catalyst, yielding six new 3-hydroxy-16,17-seco-estrone derivatives.