Total synthesis of giffonin H by fluoride-catalyzed macrocyclization
- Authors
- Park, Sooyoung; Kim, Seok-Ho; Jeong, Jin-Hyun; Shin, Dongyun
- Issue Date
- 7-Mar-2019
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.6, no.5, pp.704 - 708
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 6
- Number
- 5
- Start Page
- 704
- End Page
- 708
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/1685
- DOI
- 10.1039/c8qo01303a
- ISSN
- 2052-4129
- 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.
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