Literature DB >> 15524461

DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085.

Zeve R Akerling1, Joseph E Norton, K N Houk.   

Abstract

DFT calculations show that aromatic and bis-methoxy substituent effects in a synthetic precursor of TAN-1085 strongly favor a [1,7] sigmatropic hydrogen shift over the 6 pi electrocyclic pathway, rendering the latter unfavorable in synthesis.

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Year:  2004        PMID： 15524461     DOI： 10.1021/ol048277h

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


  4 in total

Review 1.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

2.  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

3.  Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors:  Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-04       Impact factor: 15.336

4.  Thermodynamic control of the electrocyclic ring opening of cyclobutenes: C=X substituents at C-3 mask the kinetic torquoselectivity.

Authors:  Joann M Um; Huadong Xu; K N Houk; Weiping Tang
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419
  4 in total

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