Literature DB >> 25423048

Cascade polyketide and polyene cyclizations: biomimetic total synthesis of hongoquercin B.

Tim N Barrett1, Anthony G M Barrett.   

Abstract

The total synthesis of hongoquercin B was carried out in 9 steps from trans,trans-farnesyl acetate using a palladium catalyzed decarboxylative π-farnesyl rearrangement of a diketo-dioxinone ester, aromatization and cationic diene-epoxide cyclization as key steps. This cascade tetracyclization simplifies the synthesis of terpenoid resorcylate natural products.

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Year:  2014        PMID： 25423048     DOI： 10.1021/ja511534x

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  4 in total

1.  An unusual intramolecular trans-amidation.

Authors:  Heriberto Rivera; Sachin Dhar; James J La Clair; Shiou-Chuan Tsai; Michael D Burkart
Journal:  Tetrahedron       Date:  2016-06-23       Impact factor: 2.457

2.  Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials.

Authors:  Martin Kamlar; August Runemark; Ivana Císařová; Henrik Sundén
Journal:  Org Lett       Date:  2020-10-20       Impact factor: 6.005

3.  Bioinspired synthesis of pentacyclic onocerane triterpenoids.

Authors:  Florian Bartels; Young J Hong; Daijiro Ueda; Manuela Weber; Tsutomu Sato; Dean J Tantillo; Mathias Christmann
Journal:  Chem Sci       Date:  2017-10-16       Impact factor: 9.825

4.  Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Cationic Polyene Cyclization: Total Syntheses of (+)-Hongoquercin A and B and Related Meroterpenoids.

Authors:  Tsz-Kan Ma; Daniel C Elliott; Stephanie Reid; Andrew J P White; Philip J Parsons; Anthony G M Barrett
Journal:  J Org Chem       Date:  2018-10-22       Impact factor: 4.354
  4 in total

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