Literature DB >> 15787505

Stereoselective synthesis of the octahydronaphthalene unit of integramycin via an intramolecular Diels-Alder reaction.

Thomas A Dineen1, William R Roush.   

Abstract

[reaction: see text] The racemic cis-decalin core fragment 30 of integramycin was synthesized by a sequence involving a highly diastereoselective intramolecular Diels-Alder reaction of triene 24. A remarkable switch in stereoselectivity occurred upon changing the dienophile unit of 24 from (Z)- to (E)-geometry.

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Year:  2005        PMID: 15787505     DOI: 10.1021/ol050191g

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


  2 in total

1.  Stereoselective synthesis of a model C(18)-C(35) spiroketal fragment of integramycin.

Authors:  Huikai Sun; Jason R Abbott; William R Roush
Journal:  Org Lett       Date:  2011-04-21       Impact factor: 6.005

2.  Synthesis of the spiroketal core of integramycin.

Authors:  Evgeny V Prusov
Journal:  Beilstein J Org Chem       Date:  2013-11-12       Impact factor: 2.883

  2 in total

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