Literature DB >> 10814360

Reductive aromatization of quinols: synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin.

K A Parker1, A T Georges.   

Abstract

[reaction: see text] Nucleophilic 1,2-addition of lithiated glycal 9b to functionalized quinone 7 provided, after reductive aromatization, C-arylglycoside 11b. Treatment with mCPBA afforded the tricyclic papulacandin framework. Alternatively, hydroboration gave the chaetiacandin nucleus.

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Year:  2000        PMID： 10814360     DOI： 10.1021/ol991346l

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


  4 in total

1.  TESOTf-induced rearrangement of quinols. Efficient construction of the fully functionalized carbon skeleton of the griseusins by a divergent-reconvergent approach.

Authors:  Kathlyn A Parker; Thomas L Mindt; Yung-hyo Koh
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

2.  Total Synthesis of (+)-Papulacandin D.

Authors:  Scott E Denmark; Tetsuya Kobayashi; Christopher S Regens
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

3.  Synthesis of reblastatin, autolytimycin, and non-benzoquinone analogues: potent inhibitors of heat shock protein 90.

Authors:  Iwona E Wrona; Alexander Gozman; Tony Taldone; Gabriela Chiosis; James S Panek
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

4.  Synthesis and antifungal properties of papulacandin derivatives.

Authors:  Marjolein van der Kaaden; Eefjan Breukink; Roland J Pieters
Journal:  Beilstein J Org Chem       Date:  2012-05-14       Impact factor: 2.883
  4 in total

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