Thiophene S,S-dioxides as a versatile building block for efficient complex total synthesis Kun Ho (Kenny) Park and Edward A. Anderson* University of Oxford, UK *edward.anderson@chem.ox.ac.uk The de novo synthesis of polysubstituted benzene rings is an attractive strategy that avoids the need for lengthy synthetic manipulations of pre-formed arenes. One approach to such structures involves the Diels−Alder cycloaddition/retro-cycloaddition of dienes equipped with “leaving groups” such as N 2 and CO 2 . A class of diene that has been largely overlooked to date in such chemistry are thiophene S,S-dioxides (sulfones). Herein, we will describe recent work on the first applications of thiophene S,S-dioxides as substrates for intermolecular Diels- Alder cascades in the collective synthesis of 9 members of the illudalane sesquiterpenes. 1 More interestingly, application of this chemistry in the total synthesis of various structurally complex indole alkaloids will also be discussed.
References 1. Park, K. H. (K.); Frank, N.; Duarte, F.; Anderson, E. A., J. Am. Chem. Soc. 2022 , 144 , 10017–10024.
P30
© The Author(s), 2022
Made with FlippingBook Learn more on our blog