A Biomimetic Approach to C-nor-D-homo-Steroids

Abstract
A biomimetic three-step transformation of classical "6-6-6-5"-steroids into their C-nor-D-homo-counterparts gives an easy and fast access to this highly important substructure of natural products, as it is found in cyclopamine, and nakiterpiosin. A novel reagent combination allows for the rearrangement even of 17-keto steroids with high endoselectivity. In several examples the broadness of this strategy is outlined.

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