Asymmetric synthesis of (−)-bissetone via a highly enantioselective hetero-Diels–Alder reaction

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...

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Bibliographic Details
Published in:Tetrahedron 2013-09, Vol.69 (39), p.8463-8469
Main Authors: Majer, Jakub, Jurczak, Janusz, Kwiatkowski, Piotr, Cotarca, Livius, Caille, Jean-Claude
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Bioactive natural products
Enantioselective catalysis
Hetero-Diels–Alder reaction
Tetrahydropyran-4-ones
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.048