on the occasion of his receiving the Tetrahedron Young Investigator Award Both fused and bridged tetracyclic scaffolds characteristic of endiandric acid-type natural products have been prepared in just seven steps each (longest linear sequence) from Burke's commercial cis-2-bromovinylboronic acid MIDA ester. Three iterative Suzuki-Miyaura couplings using MIDA boronates, including the first such example of a Z-Z coupling, trigger an 8/6-electrocyclization cascade. The mixture of endo and exo bicycles thus formed are elaborated into tetracycles via Horner-Wadsworth-Emmons and Diels-Alder reactions. In the process, the endo and exo diastereomers interconvert to ultimately deliver the desired products.

Direct, biomimetic synthesis of (+)-artemone via a stereoselective, organocatalytic cyclization," Nacsa, E.D.; Fielder, B.C.; Wetzler, S.P.; Srisuknimit, V.; Litz, J.P.; Van Vleet, M.J.; Quach, K.; Vosburg, D.A. Synthesis 2015

Direct, Biomimetic Synthesis of (+)-Artemone (I) via a Stereoselective, Organocatalytic Cyclization. -(NACSA, E. D.; FIELDER, B. C.; WETZLER, S. P.; SRISUKNIMIT, V.; LITZ, J. P.; VAN VLEET, M. J.; QUACH, K.; VOSBURG*, D. A.; Synthesis 47 (2015) 17, 2599-2602, http://dx.