The double annulation of tethered diacids and alkynones: History and scope

The double Michael reaction of a tethered carbon diacid (a 1,n-dinucleophile) with an alkynone (a 1,1-dielectrophile) provides highly substituted and functionalized monocyclic double Michael adducts in what is formally an [n+1] annulation. The pendant functionality in the double Michael adduct can be used to effect a second annulation. A history and overview of the "double annulation" route to bicyclic compounds is presented. The scope and selectivity of the route is also discussed. 1. Genesis of the idea 2. Exodus - time in the wasteland and ultimate redemption 3. Leviticus - laws governing the double Michael reaction 4. Numbers - diverse bicyclic compounds derived from the double Michael adducts 5. Deuteronomy - historical context and outlook.