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https://hdl.handle.net/2440/82869
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Type: | Journal article |
Title: | Biomimetic total synthesis of (±)-yezo'otogirin A |
Other Titles: | Biomimetic total synthesis of (+/-)-yezo'otogirin A |
Author: | Lam, H. Kuan, K. George, J. |
Citation: | Organic and Biomolecular Chemistry, 2014; 12(16):2519-2522 |
Publisher: | Royal Society of Chemistry |
Issue Date: | 2014 |
ISSN: | 1477-0520 1477-0539 |
Organisation: | Institute for Photonics & Advanced Sensing (IPAS) |
Statement of Responsibility: | Hiu C. Lam, Kevin K. W. Kuan and Jonathan H. George |
Abstract: | The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates. |
Keywords: | Heterocyclic Compounds, 3-Ring Molecular Conformation Stereoisomerism Biomimetic Materials |
Rights: | © Royal Society of Chemistry 2014 |
DOI: | 10.1039/c4ob00186a |
Grant ID: | http://purl.org/au-research/grants/arc/DE130100689 http://purl.org/au-research/grants/arc/DE130100689 |
Published version: | http://dx.doi.org/10.1039/c4ob00186a |
Appears in Collections: | Aurora harvest 4 IPAS publications |
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