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Synlett 2014; 25(14): 2025-2029
DOI: 10.1055/s-0034-1378380
DOI: 10.1055/s-0034-1378380
letter
A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Polyprenylated Acylphloroglucinols
Further Information
Publication History
Received: 21 March 2014
Accepted after revision: 03 June 2014
Publication Date:
23 July 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201414/lookinside/thumbnails/10.1055-s-0034-1378380-1.jpg)
Abstract
An approach to a model compound for polycyclic polyprenylated acylphloroglucinols is developed using a ring-closing metathesis approach to give a substituted cyclooctene. This undergoes cyclization via an intramolecular acylation leading to a substituted bicyclo[3.3.1]nonan-9-one related to hyperforin, nemorosone, clusianone, garsubellin A and other members of the polyprenylated acylphloroglucinol.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
References and Notes
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For reviews on the pharmacological activity of PPAPs, see:
For recent papers on the pharmacological activity of hyperforin, see:
For recent papers on the pharmacological activity of nemorosone, see:
For recent papers on the pharmacological activity of clusianone, see:
Total syntheses of PPAPs not included in ref. 3. Clusianone, see:
Nemorosone, see:
Garsubellin A, see:
For recent total syntheses of PPAPs not listed above, see:
See also:
For other examples of aldol reactions of sterically congested ester enolates with aldehydes, see:
See also:
For successful RCM, an additive was required to prevent isomerization of the starting material and product. Triphenylphosphine oxide worked best in our case. For studies on additives in RCM, see:
For the RCM of 1,9-decadiene into cyclooctene, see: