The Chemistry of the Polycyclic Polyprenylated Acylphloroglucinols
- 29 March 2012
- journal article
- review article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 51 (19), 4536-4561
- https://doi.org/10.1002/anie.201103873
Abstract
With their fascinating biological profiles and stunningly complex molecular architectures, the polycyclic polyprenylated acylphloroglucinols (PPAPs) have long provided a fertile playing field for synthetic organic chemists. In particular, the recent advent of innovative synthetic methods and strategies together with CC bond‐forming reactions and asymmetric catalysis have revitalized this field tremendously. Consequently, PPAP targets which once seemed beyond reach have now been synthesized. This Review aims to highlight the recent achievements in the total synthesis of PPAPs, as well as notable methods developed for the construction of the bicyclo[3.3.1] core of these chemically and biologically intriguing molecules.Keywords
This publication has 207 references indexed in Scilit:
- Synthetic efforts toward [3.3.1] bridged bicyclic phloroglucinol natural productsTetrahedron, 2011
- Catalytic Enantioselective Claisen Rearrangements of O‐Allyl β‐KetoestersAngewandte Chemie-International Edition, 2010
- Total Synthesis of Plukenetione AJournal of the American Chemical Society, 2010
- Catalytic Enantioselective Alkylative Dearomatization−Annulation: Total Synthesis and Absolute Configuration Assignment of Hyperibone KJournal of the American Chemical Society, 2010
- An efficient oxidative dearomatization–radical cyclization approach to symmetrically substituted bicyclic guttiferone natural productsChemical Communications, 2010
- Mechanisms of Mn(OAc)3-based oxidative free-radical additions and cyclizationsTetrahedron, 2009
- Manganese(III)-Mediated Transformations of Phloroglucinols: A Formal Oxidative [4 + 2] Cycloaddition Leading to Bicyclo[2.2.2]octadionesOrganic Letters, 2009
- The art of total synthesis through cascade reactionsChemical Society Reviews, 2009
- Enantioselective Claisen Rearrangements with a Hydrogen-Bond Donor CatalystJournal of the American Chemical Society, 2008
- Rapid Access to Polyprenylated Phloroglucinols via Alkylative Dearomatization−Annulation: Total Synthesis of (±)-ClusianoneJournal of the American Chemical Society, 2007