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

作者：Majer Jakub; Jurczak Janusz; Kwiatkowski Piotr^*; Cotarca Livius; Caille Jean Claude

来源：Tetrahedron, 2013, 69(39): 8463-8469.

DOI：10.1016/j.tet.2013.07.048

• Asymmetric synthesis
• Bioactive natural products
• Enantioselective catalysis
• Hetero-Diels-Alder reaction
• Tetrahydropyran-4-ones

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.

• 出版日期2013-9-30