Literature DB >> 20191096

Asymmetric Synthesis of the Core of AMPTD, the Key Amino Acid of Microsclerodermins F-I.

Cameron M Burnett1, Robert M Williams.   

Abstract

We report a stereoselective synthesis of the five consecutive stereocenters of AMPTD in seven steps. Highlights include an Evans glycolate aldol reaction, the use of a Weinreb amide as an aldehyde masking group, and a Mannich reaction with an Ellman-type chiral sulfimine.

Entities:  

Year:  2009        PMID： 20191096      PMCID： PMC2828631          DOI： 10.1016/j.tetlet.2009.06.144

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  3 in total

1.  Rapid assembly of the polyhydroxylated beta-amino acid constituents of microsclerodermins C, D, and E.

Authors:  Thomas Hjelmgaard; Sophie Faure; Pascale Lemoine; Bernard Viossat; David J Aitken
Journal:  Org Lett       Date:  2008-02-07       Impact factor: 6.005

2.  Anti-selective glycolate aldol additions with an oxapyrone boron enolate.

Authors:  M B Andrus; B B Sekhar; E L Meredith; N K Dalley
Journal:  Org Lett       Date:  2000-09-21       Impact factor: 6.005

3.  Asymmetric induction in methyl ketone aldol additions to alpha-alkoxy and alpha,beta-bisalkoxy aldehydes: a model for acyclic stereocontrol.

Authors:  David A Evans; Victor J Cee; Sarah J Siska
Journal:  J Am Chem Soc       Date:  2006-07-26       Impact factor: 15.419
  3 in total
  1 in total

1.  Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision.

Authors:  Ekaterina Y Melikhova; Robert D C Pullin; Christian Winter; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-15       Impact factor: 15.336
  1 in total

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