Literature DB >> 19757588

Gelsemine: a thought-provoking target for total synthesis.

Hong Lin1, Samuel J Danishefsky.   

Abstract

Gelsemine and 21-oxogelsemine have been synthesized through several routes. This Review focuses on the comparison of the different strategies to assemble the bicyclo[3.2.1]octane core, to introduce the bridgehead quaternary C20 to form the pyrrolidine moiety, to construct the oxindole residue, and to close the tetrahydropyran ring en route to gelsemine.

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Year:  2003        PMID： 19757588     DOI： 10.1002/anie.200390048

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  21 in total

1.  Total synthesis of enantiopure phalarine via a stereospecific Pictet-Spengler reaction: traceless transfer of chirality from L-tryptophan.

Authors:  John D Trzupek; Dongjoo Lee; Brendan M Crowley; Vasilios M Marathias; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

2.  Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors:  Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

3.  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

4.  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

5.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

6.  Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors:  Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

7.  Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones.

Authors:  Sandeep Rana; Amarnath Natarajan
Journal:  Org Biomol Chem       Date:  2012-11-19       Impact factor: 3.876

8.  Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

9.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

Authors:  Scott Grecian; Jeffrey Aubé
Journal:  Org Lett       Date:  2007-07-12       Impact factor: 6.005
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