Cyclohexene epoxide compounds, frequently found in natural products, exhibited wide range of interesting biological active properties. One of these natural products, epoxyquinol A and B show potent antiangiogenesis activity. Angiogenesis is a physiological process involving the growth of new blood vessels from pre-existing vessels. This process is required for invasive tumor growth and metastasis in the control of cancer progression. Thus, its inhibition can be a valuable new approach to cancer therapy.
Epoxyquinol A and B are generated from the epoxyquinol monomer (1) by oxydation and subsequent 6π-electrocyclization.The enantioselective synthesis of chiral monomer (1) of epoxyquinol A and B was achieved through a catalytic enantioselelctive Diels-Alder reaction of iodoquinonemonoketal and cyclopentadiene. We expect that this new synthetic route can be useful for the synthesis of various cyclohexene epoxide natural products.