Issue 40, 2020

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

Abstract

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Aug. 2020
Accepted
26 Sept. 2020
First published
30 Sept. 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 10939-10944

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

H. M. Chi, C. J. F. Cole, P. Hu, C. A. Taylor and S. A. Snyder, Chem. Sci., 2020, 11, 10939 DOI: 10.1039/D0SC04686H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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