Increasing the amphiphilicity of an estradiol based steroid structure by Barbier-allylation – ring-closing metathesis – dihydroxylation sequence

摘要: Abstract Polyhydroxylated steroids, such as brassinosteroids, phytoecdysteroids and steroid saponins, are structurally attractive compounds possessing a number of interesting biological properties. Accordingly, development synthetic procedures to build based structures mimicking the naturally occurring hydrophilic steroids is topical interest. In present work, d -secoestrone derivative was modified further by Barbier-allylation – ring-closing metathesis dihydroxylation sequence with aim prepare limited hydrophilicity. A straightforward synthesis route developed isolated yield for each step ranging from good excellent. All prepared were fully characterized NMR spectroscopic techniques completely assigned 1 H 13 C spectra reported herein. Finally, effects synthesized amphiphilic derivatives on proliferation cancer cells discussed.