Title of article
Asymmetric synthesis of (−)-bissetone via a highly enantioselective hetero-Diels–Alder reaction
Author/Authors
Jakub Majer، نويسنده , , Janusz Jurczak، نويسنده , , Piotr Kwiatkowski، نويسنده , , Livius Cotarca، نويسنده , , Jean-Claude Caille، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2013
Pages
7
From page
8463
To page
8469
Abstract
We demonstrate a new approach for the asymmetric synthesis of bissetone. The key reaction is the highly enantioselective hetero-Diels–Alder cycloaddition of triene 3 with ethyl glyoxylate catalyzed by readily available BINOL–Ti complexes. The HDA cycloadduct 4 was then transformed in five steps into O-protected bissetone (8) and its C5-epimer in good yield.
Keywords
Bioactive natural products , enantioselective catalysis , hetero-Diels–Alder reaction , Tetrahydropyran-4-ones , Asymmetric synthesis
Journal title
Tetrahedron
Serial Year
2013
Journal title
Tetrahedron
Record number
1106281
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