Efficient Synthesis of Bicyclo[4.4.0]decanes by Tandem Double Diels-Alder

Abstract

Polycyclic structures are frequently found in nature with specific and significant biological activity and their efficient synthesis is an important area of research. Economical syntheses have high significance in the pharmaceutical industry due to the potential to reduce step-count, waste streams, time, and money. This project’s tandem [4+2] cyclization of alkynes generates bicyclo[4.4.0]decane (cis-decalin) products in a succinct manner. The reaction includes the production of four new carbon-carbon bonds, two rings, and quaternary or vicinal quaternary centers in one pot. Successful preliminary reactions creating complex cis-decalin molecules were performed, and show promise for the synthesis of a large scope of products found in high-interest biologically active structures.