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Synthesis of Steroidal D ‐Ring‐Fused Pyrrolidines of Dehydroepiandrosterone
Author(s) -
BlancoAnia Daniel,
W. M. Aben René,
van Berkom Leon W. A.,
Scheeren Hans W.,
Rutjes Floris P. J. T.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601670
Subject(s) - chemistry , steroid , derivatization , ketone , dehydroepiandrosterone , glycidol , amine gas treating , ether , ring (chemistry) , yield (engineering) , enol , stereochemistry , organic chemistry , combinatorial chemistry , hormone , high performance liquid chromatography , androgen , biochemistry , metallurgy , catalysis , materials science
The commercially available steroid dehydroepiandrosterone 3‐acetate (DHEA) was converted into steroidal D ‐ring‐fused pyrrolidines that combine two privileged structures: a steroid and a (2‐arylethyl)amine. The three‐step transformations proceeded through conversion of the C‐17 ketone into an enol ether, followed by high‐pressure‐mediated cascade [4+2]/[3+2] cycloadditions with two nitroalkenes ([4+2]) and five dipolarophiles ([3+2]) to yield azonite intermediates. Finally, reduction of these azonites formed the new azasteroids, which are suitable for further derivatization.