Bibliographic Details
| Title: |
Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins |
| Authors: |
J. Stephen Clark, Michael Popadynec |
| Source: |
Toxins, Vol 12, Iss 12, p 740 (2020) |
| Publisher Information: |
MDPI AG, 2020. |
| Publication Year: |
2020 |
| Collection: |
LCC:Medicine |
| Subject Terms: |
pacific ciguatoxins, natural product, polycyclic ether, ring-closing metathesis, Tsuji-Trost allylation, Medicine |
| More Details: |
The I–L ring system found in all the Pacific ciguatoxins has been prepared from a tricyclic precursor in a highly stereoselective manner. Subtle differences in the reactivity of the enones present in the seven- and eight-membered rings of the tricyclic ether starting material have been exploited to allow selective protection of the enone in the eight-membered ring. Subsequent distereoselective allylation of the seven-membered ring has been accomplished by a palladium-mediated Tsuji-Trost reaction. The K-ring methyl and hydroxyl groups have been installed in a highly stereoselective manner by sequential conjugate reduction and enolate oxidation reactions. Ring L has been constructed by a use of a novel relay ring-closing metathesis reaction to complete the tetracyclic framework, which possesses the functionality necessary for elaboration of rings I and L and the introduction of ring M. |
| Document Type: |
article |
| File Description: |
electronic resource |
| Language: |
English |
| ISSN: |
2072-6651 |
| Relation: |
https://www.mdpi.com/2072-6651/12/12/740; https://doaj.org/toc/2072-6651 |
| DOI: |
10.3390/toxins12120740 |
| Access URL: |
https://doaj.org/article/c0658366520a4175a5e947023899477a |
| Accession Number: |
edsdoj.0658366520a4175a5e947023899477a |
| Database: |
Directory of Open Access Journals |
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