Literature DB >> 14723518

"Endo" and "exo" bicyclo[4.2.0]-octadiene isomers from the electrocyclization of fully substituted tetraene models for SNF 4435C and D. control of stereochemistry by choice of a functionalized substituent.

Kathlyn A Parker1, Yeon-Hee Lim.   

Abstract

[reaction: see text] A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the RZ substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.

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Year:  2004        PMID: 14723518     DOI: 10.1021/ol036048+

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


  4 in total

1.  Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary.

Authors:  Keunsoo Kim; Joseph W Lauher; Kathlyn A Parker
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  Total synthesis of kingianin A.

Authors:  Hee Nam Lim; Kathlyn A Parker
Journal:  Org Lett       Date:  2012-12-28       Impact factor: 6.005

3.  Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

Authors:  Hee Nam Lim; Kathlyn A Parker
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

4.  The total synthesis of (-)-crispatene.

Authors:  Aubry K Miller; Daniel H Byun; Christopher M Beaudry; Dirk Trauner
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-23       Impact factor: 11.205

  4 in total

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