Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A,Asian Journal of Organic Chemistry

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Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-03-13 , DOI: 10.1002/ajoc.201800025
Phongprapan Nimnual ₁ , Krissada Norseeda ₁ , Bhornrawin Akkachairin ₁ , Jumreang Tummatorn _{1,

2} , Pavitra Laohapaisan ₁ , Nantamon Supantanapong ₁ , Pennapa Chuangsoongnern ₂ , Charnsak Thongsornkleeb _{1,

3} , Satapanawat Sittihan ₁ , Somsak Ruchirawat _{1,

2} , Warabhorn Rodphon ₂

Affiliation

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.

中文翻译：

通过顺序AgTFA催化酮化-分子内羟醛缩合反应由邻炔基芳基酮合成β-萘酚和萘呋喃酮：Negundin A的总合成

已开发了以邻炔基芳基酮为底物的β-萘酚和萘[2,3 - b ]呋喃-2（3 H）-酮（萘呋喃酮）的顺序合成方法。AgTFA催化的酮化反应可在原位生成相应的1,5-二酮中间体。这些在碱性条件下通过羟醛缩合进一步环化，以中等至良好的收率获得β-萘酚产品。为了合成萘并[2,3 - b ]呋喃-2（3 H）-酮，采用了额外的内酯化步骤，从而以高收率获得了种类繁多的产品。此外，该方法也已用于合成天然产物negundinA。

更新日期：2018-03-13

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