Literature DB >> 16898833

A tether controlled exo-selective trans-annular Diels-Alder (TADA) reaction.

Wolfgang Felzmann1, Vladimir B Arion, Jean-Luc Mieusset, Johann Mulzer.   

Abstract

[reaction: see text] A fully substrate controlled stereoselective route to construct cis-hexahydronaphthalene 4 is described starting from nonracemic butenolide 6. The key step is an exo-selective transannular Diels-Alder reaction (TADA) of tetraene 5, whose intrinsic constraint allows selective formation of one stereodefined product. Compound 4 is a key intermediate in the synthesis of the novel antibiotic branimycin (1).

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Year:  2006        PMID： 16898833     DOI： 10.1021/ol061510m

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


  2 in total

1.  Studies of intramolecular Diels-Alder reactions of nitroalkenes for the stereocontrolled synthesis of trans-decalin ring systems.

Authors:  David R Williams; J Cullen Klein; Nicholas S C Chow
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Regioselective Dehydration of Sugar Thioacetals under Mild Conditions.

Authors:  Rachel Szpara; Alexander Goyder; Michael J Porter; Helen C Hailes; Tom D Sheppard
Journal:  Org Lett       Date:  2021-03-17       Impact factor: 6.005
  2 in total

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