%0 Journal Article %A George, Josemon %A Ward, Jas S. %A Sherburn, Michael S. %D 2019 %T Diene-Transmissive Diels–Alder Sequences with Benzynes %U https://acs.figshare.com/articles/journal_contribution/Diene-Transmissive_Diels_Alder_Sequences_with_Benzynes/9764873 %R 10.1021/acs.orglett.9b02807.s001 %2 https://acs.figshare.com/ndownloader/files/17493578 %K bicyclic systems %K report DTDA sequences %K multicyclic systems %K dienophile %K aryne %K dendralenic dienes %K Diel %K one-flask generation %X Diene-transmissive Diels–Alder (DTDA) sequences are extraordinarily powerful processes for the generation of fused bicyclic systems. Nonetheless, only stable dienophiles have previously been deployed. Herein we report DTDA sequences with a variety of substituted [3]­dendralenes in the first study to deploy arynes as dienophiles. We demonstrate the one-flask generation of complex, aromatic-ring-containing, multicyclic systems of relevance to medicinal chemistry. These synthetic operations provide numerous successful examples of the otherwise challenging and rarely reported intermolecular Diels–Alder reaction of acyclic 1,3-butadienes with arynes, which is made possible due to the exalted reactivity of dendralenic dienes. %I ACS Publications