Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

Sooyoung Park, Seok Ho Kim, Jin Hyun Jeong, Dongyun Shin

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)704-708
Number of pages5
JournalOrganic Chemistry Frontiers
Volume6
Issue number5
DOIs
Publication statusPublished - 2019 Mar 7

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF-2015R1D1A1A01056620, NRF-2014M3C1A3054139, NRF-2014M3A9C8024360 and NRF-2018M3A9C8024360).

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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