Nitromethane as d¹,d¹ Multiple Coupling Reagent for the Carbonyl Dianion Synthon. Practical Synthesis of Chalcogran

Abstract

The spiroacetal group is a current synthetic goal, because it is present in many biologically active natural products. A four-step synthesis of chalcogran, 1, the main component of the aggregation pheromone of the bark beetle starts from nitromethane, 1-penten-3-one, and acrolein. This synthetic approach should allow the general synthesis of 1,6-dioxaspiro[4.4]nonane derivatives.