Three-Step Synthesis of 3-Aminoseptanoside Derivatives by Using Lithiated Methoxyallene and δ-Siloxynitrones

Marcin Jasiński; Greta Utecht; Andrzej Fruziński; Hans-Ulrich Reissig

doi:10.1055/s-0035-1560398

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(06): 893-905
DOI: 10.1055/s-0035-1560398

paper

Three-Step Synthesis of 3-Aminoseptanoside Derivatives by Using Lithiated Methoxyallene and δ-Siloxynitrones

Autor*innen

Marcin Jasiński*

^aDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland eMail: mjasinski@uni.lodz.pl
Greta Utecht

^aDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland eMail: mjasinski@uni.lodz.pl
Andrzej Fruziński

^bInstitute of General and Ecological Chemistry, Łódź University of Technology, Żeromskiego 115, 90-924 Łódź, Poland
Hans-Ulrich Reissig

^cInstitut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany eMail: hans.reissig@chemie.fu-berlin.de

Abstract

Alle Artikel dieser Rubrik

Dedicated to Professor Grzegorz Mlostoń on the occasion of his 65^th birthday

Abstract

A three-step approach to enantiomerically pure 3-aminoseptanoside derivatives by addition of lithiated methoxyallene to δ-silylated aldopentose-derived nitrones, followed by Brønsted acid mediated cyclization and chemoselective N–O bond scission is presented. For the addition of the methoxyallene anion leading to 3,6-dihydro-1,2-oxazines, excellent syn-diastereoselectivities were observed in the case of d-xylose- and l-arabinose-derived nitrones, whereas the d-ribose analogue provided syn- and anti-configured products in an approximately 2:1 ratio. Subsequent proton-induced reactions provided the corresponding dimethyl ketals as kinetic products, which slowly converted into bicyclic oxepanoides formed in a highly cis-selective manner. The final reductive ring opening was performed in good yields by using an excess of samarium(II) iodide. With a selected compound it was demonstrated that this type of product is a suitable precursor for the preparation of polyfunctionalized oxepanopyrrolidine derivatives.

Key words

allenes - nitrones - heterocycles - 1,2-oxazines - oxepanes - septanosides

Volltext

Referenzen

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