Literature DB >> 16623580

Synthesis of the 3-aza-[7]-paracyclophane core of haouamine A and B.

Peter Wipf1, Markus Furegati.   

Abstract

[reaction: see text] The synthesis of the highly strained 3-aza-[7]-paracyclophane core of haouamines A and B is based on a macrocyclization-aromatization protocol, allowing for a stepwise increase in ring strain and establishing the oxygenation pattern of the natural products.

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Year:  2006        PMID： 16623580     DOI： 10.1021/ol060455e

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


  8 in total

1.  Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

Authors:  Erik Fenster; Charlie Fehl; Jeffrey Aubé
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A.

Authors:  Jeannie H Jeong; Steven M Weinreb
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

3.  Strained cyclophane macrocycles: impact of progressive ring size reduction on synthesis and structure.

Authors:  Andrew R Bogdan; Steven V Jerome; K N Houk; Keith James
Journal:  J Am Chem Soc       Date:  2012-01-23       Impact factor: 15.419

4.  Total synthesis of haouamine A: the indeno-tetrahydropyridine core.

Authors:  Noah Z Burns; Mikkel Jessing; Phil S Baran
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

5.  Chemoselectivity: the mother of invention in total synthesis.

Authors:  Ryan A Shenvi; Daniel P O'Malley; Phil S Baran
Journal:  Acc Chem Res       Date:  2009-04-21       Impact factor: 22.384

6.  A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.

Authors:  Filip Petronijevic; Cody Timmons; Anthony Cuzzupe; Peter Wipf
Journal:  Chem Commun (Camb)       Date:  2008-11-11       Impact factor: 6.222

7.  Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

Authors:  Noah Z Burns; Irina N Krylova; Rami N Hannoush; Phil S Baran
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

8.  5-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition.

Authors:  Matthew LaPorte; Ki Bum Hong; Jie Xu; Peter Wipf
Journal:  J Org Chem       Date:  2012-11-16       Impact factor: 4.354
  8 in total

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