Abstract
A stereocontrolled synthesis of the hitherto unknown (±)-6,7-dideoxyforskolin has been accomplished, incorporating controlled C-ring annulation with simultaneous creation of the stereogenic center at C-13 via oxymercuration. An alternative attempt at C-ring elaboration via conjugate addition of a higher order vinyl cuprate reagent to dihydropyran-4-one resulted in the exclusive formation of its 13-epimer. These analogues displayed no ability to stimulate adenytate cyclase in rat cerebral cortical membranes.
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