Literature DB >> 10540398

Total Synthesis of (+/-)-Gelsemine.

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Abstract

A complex molecular reorganization (1-->2), a sequential anionic aza-Cope rearrangement and Mannich cyclization, and an unprecedented intramolecular Heck reaction of the tetrasubstituted double bond of a vinylogous carbamate are key steps in a new total synthesis of (+/-)-gelsemine (3). MOM=methoxymethyl, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene.

Entities:  

Year:  1999        PMID： 10540398

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


  5 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 Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Authors:  Eric T Newcomb; Phil C Knutson; Blaine A Pedersen; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2015-12-30       Impact factor: 15.419

4.  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

5.  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
  5 in total

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