Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis
Name
nihms942972.pdf
Description
Accepted version
Size
1.34 MB
Format
Adobe PDF
Checksum (MD5)
6c8d2bc99e8ee60b7bdf6c3d9157d7f1
Author(s)
Katcher, Matthew Herman
Jamison, Timothy F
Date Issued
March 2018
Journal
Tetrahedron
Publisher
Elsevier BV
Citation
Katcher, Matthew H., and Timothy F. Jamison, "Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis." Tetrahedron 74, 11 (Mar. 2018): p. 1111-22 doi 10.1016/J.TET.2018.01.039 ©2018 Author(s)
Version
Author's final manuscript
Abstract
Shortly after the initial isolation of marine ladder polyether natural products, biomimetic epoxide-opening cascade reactions were proposed as an efficient strategy for the synthesis of these compounds. However, difficulties in assembling the cascade precursors have limited the realization of these cascades. In this report, we describe strategies that provide convergent access to cascade precursors via regioselective allylation and efficient fragment coupling. We then investigate epoxide-opening cascades promoted by strong bases for the formation of fused tetrahydropyrans. These strategies are evaluated in the context of the synthesis of rings CDEFG of brevisulcenal F.
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.TET.2018.01.039
