Beilstein Arch. 2026, 202618. https://doi.org/10.3762/bxiv.2026.18.v1
Published 29 May 2026
With the aim to develop efficient synthetic routes to 7,8-substituted aryl-naphthalene lignans and structural analogs via a Photo-Dehydro-Diels-Alder reaction as key step, three different approaches were investigated. The first strategy is based on the presence of electron-withdrawing groups (EWG) as placeholder for alkoxy groups (EWG strategy). Although two lignan analogs (19, 20) could be prepared the EWG strategy was not an optimum solution. The second strategy takes advantage of different sizes of meta-substituents to force the formation of 7,8-substituted products (meta-directing strategy). Here, a sufficient large size difference is mandatory. While the combination TMS/OMe works very well and provided the access to natural product analogs 29 and 30, the combination TMS/OBn completely failed. The third and most successful approach is based on blocking ortho-positions with the bulky TMS group (ortho-blocking strategy). By using this method, the natural products helioxanthin 1 and retrohelioxanthin 2 could be successfully synthesized.
Keywords: Lignans; Natural products; Total synthesis; Photochemistry; Naphthalenes
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Wessig, P.; Wichterich, L.; Sperlich, E.; Kelling, A. Beilstein Arch. 2026, 202618. doi:10.3762/bxiv.2026.18.v1
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