From Cyclopropene to Housane Derivatives Via Intramolecular Cyclopropanation
Darío Coto, David Suárez‐García, Sergio Mata, Israel Fernández, Luís A. López, R. Vicente
Abstract
The synthesis of housane derivatives from cyclopropenes is described. Under rhodium(II) catalysis, cyclopropenylvinyl carbinols can regioselectively generate a carbene intermediate which undergoes an intramolecular cyclopropanation to form a housane, a skeleton with similar ring strain as the cyclopropene precursor. The procedure shows a remarkable broad scope and efficiency. Moreover, the method served to prepare man-made housane-containing terpene derivatives, which are not accessible by Nature.
Topics & Concepts
CyclopropeneCyclopropanationIntramolecular forceCarbeneChemistryRhodiumRing strainRing (chemistry)CatalysisStereochemistryCombinatorial chemistryOrganic chemistryCyclopropane Reaction MechanismsSynthesis and Reactivity of HeterocyclesCancer Treatment and Pharmacology