Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications

The recent natural product isolates spiroviolene and spirograterpene A are two relatively non-functionalized linear triquinane terpenes with a large number of structural homologies. Nevertheless, three significant areas of structural disparity exist based on their original assignments, one of which...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-10, Vol.11 (4), p.1939-1944
Main Authors: Chi, Hyung Min, Cole, Charles J. F, Hu, Pengfei, Taylor, Cooper A, Snyder, Scott A
Format: Article
Language:English
Subjects:
Chemistry
Divergence
Homology
Natural products
Terpenes
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Summary:The recent natural product isolates spiroviolene and spirograterpene A are two relatively non-functionalized linear triquinane terpenes with a large number of structural homologies. Nevertheless, three significant areas of structural disparity exist based on their original assignments, one of which implies a key stereochemical divergence early in their respective biosyntheses. Herein, using two known bicyclic ketone intermediates, a core Pd-catalyzed Heck cyclization sequence, and several chemoselective transformations, we describe concise total syntheses of both natural product targets and propose that the structure of spiroviolene should be reassigned. As a result, these natural products possess greater homology than previously anticipated. Concise syntheses of spiroviolene and spirograterpene A have been achieved from a common intermediate, indicating a structure revision of one is necessary along with implications for its biosynthesis.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc04686h