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Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

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Abstract

The first total synthesis of giffonin H, a highly strained 15-membered macrocyclic diaryl ether, has been achieved in eight linear steps with 10% overall yield. Key steps include Ullmann cross coupling, (Z)-selective Julia–Kocienski olefination, and fluoride-mediated macrocyclization of TMS-alkyne and aldehyde. In particular, the strategy used for macrocyclization is an unprecedented and unique synthetic approach for cyclic diarylheptanoids. The fluoride-mediated macrocyclization strategy should be applicable to the synthesis of giffonin congeners under mild reaction conditions without affecting the integrity of subtle diene moieties.

Graphical abstract: Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

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Publication details

The article was received on 04 Dec 2018, accepted on 17 Jan 2019 and first published on 18 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01303A
Citation: Org. Chem. Front., 2019, Advance Article

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    Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

    S. Park, S. Kim, J. Jeong and D. Shin, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01303A

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