Literature DB >> 18980328

Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols.

Ryukichi Takagi1, Yuta Inoue, Katsuo Ohkata.   

Abstract

The construction of a highly functionalized adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols (PPAPs) is described. The method features the construction of the bicyclo[3.3.1]nonane core (3) by successive Michael reactions and the construction of the adamantane core of plukenetione-type PPAPs by acid-catalyzed cyclization of a bicyclo[3.3.1]nonane precursor (2).

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Year:  2008        PMID： 18980328     DOI： 10.1021/jo801595y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

Review 1.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

2.  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

3.  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

4.  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 in total

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