Literature DB >> 14583006

A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine.

Anthony J Pearson1, Xiaolong Wang.   

Abstract

A convenient one-pot procedure to prepare angularly substituted bicyclic and tricyclic molecules with excellent diastereoselectivity in good yield was developed, by Fe(CO)5 promoted cyclization. Three transformations (complexation, isomerization, and cyclization) were realized in a single operation. The product of this reaction may be a precursor for synthesis of the alkaloid gelsemine.

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Year:  2003        PMID： 14583006     DOI： 10.1021/ja030407e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  3 in total

1.  Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.

Authors:  Andrew Madin; Christopher J O'Donnell; Taeboem Oh; David W Old; Larry E Overman; Matthew J Sharp
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

2.  Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.

Authors:  William G Earley; Jon E Jacobsen; Andrew Madin; G Patrick Meier; Christopher J O'Donnell; Taeboem Oh; David W Old; Larry E Overman; Matthew J Sharp
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

3.  Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach.

Authors:  Xiaoming Chen; Shengguo Duan; Cheng Tao; Hongbin Zhai; Fayang G Qiu
Journal:  Nat Commun       Date:  2015-05-21       Impact factor: 14.919
  3 in total

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