Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 5, Pages 1247-1251Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304110
Keywords
chiriquitoxin; natural products; Pummerer rearrangement; tetrodotoxin; total synthesis
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Funding
- MEXT
- Sumitomo Foundation
- Yamada Science Foundation
- Daiichi Sankyo Foundation of Life Science
- SUNBOR GRANT from the Suntory Institute for Bioorganic Research
- Grants-in-Aid for Scientific Research [23102015, 24580161] Funding Source: KAKEN
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The first total synthesis of chiriquitoxin, the most structurally complex analogue of tetrodotoxin isolated from a Costa Rican dart frog, has been accomplished from a newly designed intermediate for a variety of tetrodotoxin derivatives. The synthesis includes the third total synthesis of tetrodotoxin in this laboratory, and its intermediate was transformed into chiriquitoxin by a stereocontrolled aldol reaction with a D-camphor-derived lactone for installation of the unique side chain, and a new deprotection of methylthiomethyl (MTM) ether by using a Pummerer rearrangement.
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