Organic Chemistry Seminar

The two simplest acyclic branched structures comprising only conjugated C=C units, namely [3]dendralene (3-methylene-1,4-pentadiene) and [4]dendralene (3,4-dimethylene-1,5-hexadiene), were first reported in 1955 and 1962, respectively. No higher members of the series were described in the literature until the year 2000. We have played a dominant role in the push for a deeper understanding of these compounds and their synthetic potential. This greater appreciation of C=C bond rich systems has led to the successful synthesis of many unprecedented structures, including [5]radialene, the simplest cyclic branched pentaene. This presentation will focus on various aspects of the chemistry involved in the preparation of branched C=C bond rich compounds, and their deployment in the most step economic total syntheses of natural products.