Literature DB >> 18254636

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

Thomas Hjelmgaard1, Sophie Faure, Pascale Lemoine, Bernard Viossat, David J Aitken.   

Abstract

A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

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Year:  2008        PMID: 18254636     DOI: 10.1021/ol702962z

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


  4 in total

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

Authors:  Cameron M Burnett; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

2.  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

3.  Tethered aminohydroxylation: synthesis of the β-amino acid of microsclerodermins A and B.

Authors:  Robert D C Pullin; Akshat H Rathi; Ekaterina Y Melikhova; Christian Winter; Amber L Thompson; Timothy J Donohoe
Journal:  Org Lett       Date:  2013-10-16       Impact factor: 6.005

4.  Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils.

Authors:  Dan E Adolfsson; Mohit Tyagi; Pardeep Singh; Adrian Deuschmann; Jörgen Ådén; Anna L Gharibyan; Sanduni Wasana Jayaweera; Anders E G Lindgren; Anders Olofsson; Fredrik Almqvist
Journal:  J Org Chem       Date:  2020-10-25       Impact factor: 4.354

  4 in total

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