Abstract
AbstractThe commercially available steroid dehydroepiandrosterone 3‐acetate (DHEA) was converted into new, highly functionalized spiro derivatives by modification of the D‐ring. The transformation proceeded through conversion of the C‐17 carbonyl group into an electron‐deficient alkene, followed by either [2+2] or [4+2] cycloaddition. The cycloaddition reactions were successful for alkylidene malononitriles and 2‐cyano acrylates. Application of high pressure (15 kbar) was essential for good conversions due to the high steric hindrance on position C‐17. The cycloadducts formed from the reaction of 2‐cyano acrylates and Danishefsky's diene have high potential for further functionalization.
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