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
Main Authors: Sittihan, Satapanawat (Author), Jamison, Timothy F (Author)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2020-07-22T20:41:47Z.
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Online Access:Get fulltext
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100 1 0 |a Sittihan, Satapanawat  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
700 1 0 |a Jamison, Timothy F  |e author 
245 0 0 |a Total Synthesis of the Marine Ladder Polyether Gymnocin B 
260 |b American Chemical Society (ACS),   |c 2020-07-22T20:41:47Z. 
856 |z Get fulltext  |u https://hdl.handle.net/1721.1/126328 
520 |a 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. 
520 |a NIGMS (GM072566) 
546 |a en 
655 7 |a Article 
773 |t Journal of the American Chemical Society