Journal or Book Title
The Journal of Organic Chemistry
The anticancer agent rocaglamide contains a novel bicyclo[3.3.0]octanol structure. The approach to this molecule involved the preparation of a hydroxy ketone intermediate via a samarium-mediated cyclization. This ketone was then converted into an excellent Michael acceptor via novel chemistry. Subsequent steps led to the preparation of an isomer of rocaglamide. An X-ray determination supported our view that cuprate addition occurred with unusual concave selectivity.
American Chemical Society
Kraus, George A. and Sy, James O., "A synthetic approach to rocaglamide via reductive cyclization of 𝛿-keto nitriles" (1989). Chemistry Publications. 641.