期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 18, 页码 3279-3282出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100317
关键词
Enantioselectivity; Asymmetric synthesis; Steroids; Cycloaddition; Rearrangement
资金
- Ministry of Education, Youth and Sports of the Czech Republic [1M0508, MSM0021620857]
Enantioselective synthesis of unnatural (-)-methoxyestrone in 12 steps from the commercially available tetralone based on the formation of a chiral bicyclic intermediate having the A-B steroid ring framework was accomplished. The crucial synthetic step comprised the enantioselective conjugate addition of vinylmagnesium bromide to a chiral imine formed from a trisubstituted cyclic alpha,beta-unsaturated aldehyde with >98% ee, giving rise to the stereoselectively substituted building block possessing the A-B steroid rings. Further steps included the construction of the side chain containing the triple bond, and the obtained enyne was subjected to a Pauson-Khand reaction that furnished stereoselectively an intermediate tetracyclic ketone. Further functional group transformations yielded the target compound.
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