5 years ago

A Unified Modular Synthetic Strategy for Dictyodendrins F, H, I, and G

A Unified Modular Synthetic Strategy for Dictyodendrins F, H, I, and G
Yun He, Jian Guo, Wenxi Li, Sreenivas Banne, D. Prabhakar Reddy, Chenhui Wang
A unified modular synthetic strategy has been developed for the first total synthesis of dictyodendrins G and synthesis of dictyodendrin F, H and I in 11 steps. The synthesis features consecutive functionalization of the core aminoquinone by palladium-mediated Suzuki–Miyaura coupling reaction, 1,4-addition, acylation and base mediated formation of a pyrrolinone, and the formation of carbazolequinone moiety through a formal [3 + 2] cycloaddition using arynes generated in situ. Several dictyodendrin analogues were also synthesized using this strategy.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02511

DOI: 10.1021/acs.orglett.7b02511

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