Total Synthesis of Aspergillides Using a Transannular Oxy-Michael Strategy
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- Shishido Kozo
- Graduate School of Pharmaceutical Sciences, The University of Tokushima
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Abstract
In this account, full details of our total synthetic studies on aspergillides A, B and C, which have been isolated from the marine-derived fungus Aspergillus ostianus strain 01F313, are presented. The highly diastereoselective constructions of tri- and tetra-substituted tetrahydropyrans employing intramolecular oxy-Michael (IMOM) reactions have been developed and successfully applied to the first generation total syntheses of aspergillides A and C. However, the longer reaction steps and lower overall yields prompted us to try and devise a general methodology that would be useful for a highly efficient synthesis of all the aspergillides. To this end, a biomimetic [6-exo-trig] transannular oxy-Michael (TAOM) strategy was invented and successfully and efficiently applied to the second generation total syntheses of aspergillides A, B and C. Ultimately, the cycloaddition was controlled by using more suitable conditions, and aspergillide A/B and aspergillide C/3-epi-aspergillide C were able to be synthesized from a common precursor. In addition, successful conversions of aspergillide A to aspergillide B and 3-epi-aspergillide C to aspergillide C were demonstrated for the first time during these synthetic studies.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 70 (11), 1196-1205, 2012
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001205339308416
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- NII Article ID
- 10031131199
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC38XhslCjt7bP
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 024087992
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed