Total Synthesis of the Marine Ladder Polyether Gymnocin B
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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.
Date issued
2019-07Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
1520-5126