Literature DB >> 19739652

A short biomimetic approach to the fully functionalized bicyclic framework of type A acylphloroglucinols.

Elias A Couladouros1, Marianna Dakanali, Konstantinos D Demadis, Veroniki P Vidali.   

Abstract

A biomimetic approach toward type A polyprenylated acylphloroglucinols (PPAPs) is described. The method is based on a C-alkylation-cation cyclization reaction sequence, leading to a convenient buildup of molecular complexity, employing the simple and readily available deoxycohumulone and an appropriately functionalized hydroxy halide. Thus, a versatile construction of the fully functionalized bicyclic framework of type A PPAPs (5) was achieved.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19739652     DOI: 10.1021/ol901781n

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Total synthesis of plukenetione A.

Authors:  Qiang Zhang; Branko Mitasev; Ji Qi; John A Porco
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

2.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

3.  Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products.

Authors:  Jon T Njardarson
Journal:  Tetrahedron       Date:  2011-10-07       Impact factor: 2.457

4.  Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation.

Authors:  Alexander J Grenning; Jonathan H Boyce; John A Porco
Journal:  J Am Chem Soc       Date:  2014-08-07       Impact factor: 15.419

5.  Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds.

Authors:  Jonathan H Boyce; Benjamin J Reisman; Brian O Bachmann; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336

6.  Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines - application to a formal synthesis of sarizotan.

Authors:  Wafa Gati; Mohamed M Rammah; Mohamed B Rammah; Gwilherm Evano
Journal:  Beilstein J Org Chem       Date:  2012-12-21       Impact factor: 2.883

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.