A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Poly­prenylated Acylphloroglucinols

Stefanie Schmitt; Eva Feidt; David Hartmann; Volker Huch; Johann Jauch

doi:10.1055/s-0034-1378380

Synlett, Table of Contents

Synlett 2014; 25(14): 2025-2029
DOI: 10.1055/s-0034-1378380

letter

A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Polyprenylated Acylphloroglucinols

Authors

Stefanie Schmitt

^aInstitut für Organische Chemie II, Universität des Saarlandes, 66123 Saarbrücken, Germany
Eva Feidt

^aInstitut für Organische Chemie II, Universität des Saarlandes, 66123 Saarbrücken, Germany
David Hartmann

^aInstitut für Organische Chemie II, Universität des Saarlandes, 66123 Saarbrücken, Germany
Volker Huch

^bInstitut für Anorganische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany Fax: +49(681)30264151 Email: j.jauch@mx.uni-saarland.de
Johann Jauch*

^aInstitut für Organische Chemie II, Universität des Saarlandes, 66123 Saarbrücken, Germany

Abstract

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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.

Key words

bicyclic compounds - natural products - metathesis - alkene acylation - steric hindrance

Full Text

References

References and Notes

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A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Poly­prenylated Acylphloroglucinols

Authors

A Metathesis–Acylation Approach to the Bicyclic Core of Polycyclic Polyprenylated Acylphloroglucinols