Total Synthesis of the Marine Ladder Polyether Gymnocin B

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, coalesce...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-07, Vol.141 (28), p.11239-11244
Main Authors: Sittihan, Satapanawat, Jamison, Timothy F
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b04696