Revisiting the stereochemistry of hydrindanes via catalytic hydrogenation of hydrindenes and synthesis of cis/trans-7-oxa-estra-4,9-diene-3,17-diones

ORGN 780

Fu-An Kang, fkang@prdus.jnj.com, Nareshkumar Jain, and Zhihua Sui. Johnson & Johnson Pharmaceutical Research and Development, LLC, 665 Stockton Drive, Exton, PA 19341
The construction of the trans-hydrindane portion of steroids, vitamin D, higher terpenes and related natural products has been a long-standing challenge in synthetic organic chemistry. Catalytic hydrogenation of hydrindenes has appeared to be a convenient approach for the creation of the hydrindane system. However, there have been conflicting reports on the stereochemical outcomes of hydrindanes via catalytic hydrogenation of hydrindenes. We will present the study of catalytic hydrogenation of hydrindenes with an oxygen-containing side-chain on the enone system, as well as structural elucidation of the stereochemistry by X-ray crystallography. On the basis of construction of both cis- and trans-O-alkylated-hydrindanes, stereoselective synthesis of cis- and trans-7-oxa-estra-4,9-diene-3,17-diones will be discussed.