Literature DB >> 12967309

Bridgehead arylation: a direct route to advanced intermediates for the synthesis of C-20 diterpene alkaloids.

Craig M Williams1, Lewis N Mander.   

Abstract

[reaction: see text] Rapid access to the ABCE ring system of the C(20) diterpene alkaloids was achieved by silver(I)-promoted intramolecular Friedel-Crafts arylation of a functional group-specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative.

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Year:  2003        PMID： 12967309     DOI： 10.1021/ol0353060

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


  5 in total

1.  Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions.

Authors:  Kevin M Peese; David Y Gin
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

2.  Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition.

Authors:  Kevin M Peese; David Y Gin
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

3.  A model study toward the total synthesis of N-deacetyllappaconitine.

Authors:  Douglass F Taber; Jiang-Lin Liang; Bei Chen; Lisi Cai
Journal:  J Org Chem       Date:  2005-10-28       Impact factor: 4.354

4.  Gallium(III)-catalyzed cycloisomerization approach to the diterpenoid alkaloids: construction of the core structure for the hetidines and hetisines.

Authors:  Amy M Hamlin; Felipe de Jesus Cortez; David Lapointe; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-26       Impact factor: 15.336

5.  Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine.

Authors:  Kevin M Peese; David Y Gin
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
  5 in total

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