A Method to Access Highly Functionalized Dibenzobicyclo[3.2.1]octadienones: Application to the Construction of the 6/6/5/6/6 Carbon Skeleton of Rubialatin A
Gurupada Hazra, Gitanjali Mishra, Rambabu Dandela, Barla Thirupathi
Abstract
The dibenzobicyclo[3.2.1]octadienone scaffold, which has been found in naphthocyclinones, engelharquinones, rubialatin A, etc., has been synthesized under mild transition metal-free conditions by aryne insertion reaction with 2-keto-1,3-indandiones. The application of this methodology has been demonstrated for the synthesis of the 6/6/5/6/6 scaffold of rubialatin A. 1H NMR experimental studies confirm that the reaction proceeds through the formation of benzocyclobutane followed by a 7-member carbocycle ring.
Topics & Concepts
ChemistryAryneRing (chemistry)Carbon skeletonScaffoldTransition metalCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisMedicineBiomedical engineeringCyclization and Aryne ChemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloids