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Synlett
DOI: 10.1055/s-0043-1773544
DOI: 10.1055/s-0043-1773544
letter
Synthetic Studies toward 4,9-Anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a Proposed Biosynthetic Precursor of Tetrodotoxin
This research was supported in part by the Japan Society for the Promotion of Science (JSPS), KAKENHI [Grant-in-Aid for Early-Career Scientists (22K20571), Grant-in-Aid for Scientific Research (B) (24K01636), Grant-in-Aid for Transformative Research Areas (A) (23H04553), and Grant-in-Aid for Scientific Research(A) (23H00347)] from the Ministry of Education, Culture, Sports, Science and Technology (MEXT).
Abstract
We report the synthesis of the 8-epi analogue of 4,9-anhydro-10-hemiketal-5-deoxytetrodotoxin, a proposed biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt Cynops ensicauda popei, from a previously reported protected amine via stereoselective hydroxylation of the bicyclic carbocycle.
Key words
tetrodotoxin - biosynthesis - chemical synthesis - natural products - stereoselective oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773544.
- Supporting Information
Publication History
Received: 21 February 2025
Accepted after revision: 07 April 2025
Article published online:
27 May 2025
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