4.8 Article

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

Journal

ORGANIC LETTERS
Volume 19, Issue 18, Pages 4996-4999

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02511

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Funding

  1. National Natural Science Foundation of China [21572027, 21372267]

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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] cydoaddition using arynes generated in situ. Several dictyodendrin analogues were also synthesized using this strategy.

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