One-Pot Organocatalytic Enantioselective Michael–Michael–Aldol–Henry
Reaction Cascade. A Facile Entry to the Steroid System with Six Contiguous
Stereogenic Centers
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Abstract
An
expedited method has been developed for the enantioselective
synthesis of highly functionalized steroid systems containing six
contiguous stereogenic centers with high enantioselectivities (99% <i>ee</i>). The one-pot methodology comprises a cascade of organocatalytic
Michael–Michael–aldol–Henry reactions of 7-nitrohept-3-en-2-one
and 5-(1-methyl-2,5-dioxocyclopentyl)pent-2-enal.
The structure and absolute configuration of the products were confirmed
by X-ray analyses of appropriate products