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- Title
Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A.
- Authors
Nimnual, Phongprapan; Norseeda, Krissada; Akkachairin, Bhornrawin; Tummatorn, Jumreang; Laohapaisan, Pavitra; Supantanapong, Nantamon; Chuangsoongnern, Pennapa; Thongsornkleeb, Charnsak; Sittihan, Satapanawat; Ruchirawat, Somsak; Rodphon, Warabhorn
- Abstract
Abstract: A sequential synthesis of β‐naphthols and naphtho[2,3‐b]furan‐2(3H)‐ones (naphthofuranones) has been developed using ortho‐alkynylarylketones as the substrates. The AgTFA‐catalyzed ketonization generated the corresponding 1,5‐diketone intermediates in situ; these were further cyclized via aldol condensation under basic conditions to obtain β‐naphthol products in moderate to good yields. For the synthesis of naphtho[2,3‐b]furan‐2(3H)‐ones, an additional lactonization step was applied to give a broad range of products in good yields. Moreover, this method has also been utilized in the synthesis of natural product negundin A.
- Subjects
FURANONE synthesis; ALDOL condensation; INTRAMOLECULAR forces
- Publication
Asian Journal of Organic Chemistry, 2018, Vol 7, Issue 5, p932
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201800025