Total Synthesis of the Marine Ladder Polyether Gymnocin B
Name
nihms-1055336.pdf
Description
Accepted version
Size
1.99 MB
Format
Adobe PDF
Checksum (MD5)
4de8558f488c8e9148c0a3f394938c13
Author(s)
Sittihan, Satapanawat
Jamison, Timothy F
Date Issued
July 2019
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Sittihan, Satapanawat and Timothy F. Jamison, "Total Synthesis of the Marine Ladder Polyether Gymnocin B." Journal of the American Chemical Society 141, 28 (July 2019): p. 11239–244 doi. 10.1021/jacs.9b04696 ©2019 Authors
Version
Author's final manuscript
Abstract
Herein, we report the first total synthesis of marine ladder polyether gymnocin B (1) based on a two-phase strategy. In Phase I, inspired by the proposed biosynthesis, epoxide-opening cascades assemble 10 out of 15 cyclic ether rings making up the molecular core. In the subsequent Phase II, coalescence elevates the molecular complexity further by coupling of these subunits. Our two-phase synthetic approach significantly improved the step efficiency of the synthesis of this class of natural products. ©2019 American Chemical Society.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.9B04696
