Synthesis of β-Hydroxynaphthoate Derivatives from Ketodioxinones via Benzyne Acyl-Alkylation and Aldol Condensation Cascade

Hiroshi Takikawa; Arata Nishii; Keisuke Suzuki

doi:10.1055/s-0035-1562514

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(19): 3331-3338
DOI: 10.1055/s-0035-1562514

paper

Synthesis of β-Hydroxynaphthoate Derivatives from Ketodioxinones via Benzyne Acyl-Alkylation and Aldol Condensation Cascade

Authors

Hiroshi Takikawa

Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan eMail: ksuzuki@chem.titech.ac.jp
Arata Nishii

Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan eMail: ksuzuki@chem.titech.ac.jp
Keisuke Suzuki*

Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan eMail: ksuzuki@chem.titech.ac.jp

Abstract

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Dedicated to the memory of Prof. Jean F. Normant

Abstract

A variety of highly functionalized β-hydroxynaphthoate derivatives are prepared by a two-step protocol: (1) acyl-alkylation of benzynes with ketodioxinones and (2) intramolecular aldol condensation. The substitution pattern of the products is related to polycyclic natural products derived from the type-II polyketide biosynthesis.

Key words

ketodioxinones - benzynes - acyl-alkylation - aldol condensation - cascade reaction

Volltext

Referenzen

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