Synthesis of the ABC framework of tamulamides A and B
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nihms-1042298.pdf
Description
Accepted version
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733.98 KB
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Adobe PDF
Checksum (MD5)
2612fe43a70e2a417b08dfe9e27018fa
Author(s)
Kelley, Elizabeth H. (Elizabeth Helen)
Jamison, Timothy F
Date Issued
October 2018
Journal
Bioorganic & Medicinal Chemistry
Publisher
Elsevier BV
Citation
Kelley, Elizabeth H., and Timothy F. Jamison, "Synthesis of the ABC framework of tamulamides A and B." Bioorganic & Medicinal Chemistry 26, 19 (Oct. 2018): 5327-35 doi 10.1016/J.BMC.2018.04.046 ©2018 Author(s)
Version
Author's final manuscript
Abstract
Synthesis of the fused tetrahydrofuran motif comprising the ABC rings of the marine ladder polyethers tamulamides A and B has been achieved via two different polyepoxide cascade strategies. Investigations into a triepoxide cascade under aqueous conditions revealed the importance of the electronic nature of the cascade end-group with this initial approach. Ultimately, a diepoxide cascade under basic conditions proved most successful, providing the ABC tetrahydropyran triad in 41% yield.
Description
Part of special issue: Symposium in Print in honour of Laura Kiessling, Tetrahedron Prize for Creativity in Organic Chemistry 2017.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1016/J.BMC.2018.04.046
