Literature DB >> 19860384

Efficient formal total synthesis of the erythrina alkaloid (+)-erysotramidine, using a domino process.

Lutz F Tietze1, Nina Tölle, Daniel Kratzert, Dietmar Stalke.   

Abstract

A domino process consisting of an amidation, spirocyclization, and formation of an iminium ion and electrophilic aromatic substitution of a phenylethylamine and a ketoester leads to the spirocyclic skeleton of (+)-erysotramidine, which can be further transformed into the natural alkaloid.

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Year:  2009        PMID: 19860384     DOI: 10.1021/ol901980u

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


  4 in total

1.  Total synthesis of (±)-isophellibiline.

Authors:  Raymond L Funk; Johannes Belmar
Journal:  Tetrahedron Lett       Date:  2012-01-11       Impact factor: 2.415

2.  Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

Authors:  Jung Min Joo; Ramoncito A David; Yu Yuan; Chulbom Lee
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by Cu complexes of chiral N-heterocyclic carbenes.

Authors:  Kang-Sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

4.  Metal-free catalytic C-Si bond formation in an aqueous medium. Enantioselective NHC-catalyzed silyl conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.

Authors:  Jeannette M O'Brien; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

  4 in total

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