Synthesis of β-Naphthols and Naphthofuranones from ortho-Alkynylarylketones via Sequential AgTFA-Catalyzed Ketonization-Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

被引：11

作者：

Nimnual, Phongprapan ^{[1
]}

Norseeda, Krissada ^{[1
]}

Akkachairin, Bhornrawin ^{[1
]}

Tummatorn, Jumreang ^{[1
,2
]}

Laohapaisan, Pavitra ^{[1
]}

Supantanapong, Nantamon ^{[1
]}

Chuangsoongnern, Pennapa ^{[2
]}

Thongsornkleeb, Charnsak ^{[1
,3
]}

Sittihan, Satapanawat ^{[1
]}

Ruchirawat, Somsak ^{[1
,2
]}

Rodphon, Warabhorn ^{[2
]}

机构：

[1] Minist Educ, Program Chem Biol, Chulabhorn Grad Inst, Ctr Excellence Environm Hlth & Toxicol EHT, 54 Kamphaeng Phet 6,Laksi, Bangkok 10210, Thailand

[2] Chulabhorn Res Inst, Lab Med Chem, 54 Kamphaeng Phet 6,Laksi, Bangkok 10210, Thailand

[3] Chulabhorn Res Inst, Lab Organ Synth, 54 Kamphaeng Phet 6,Laksi, Bangkok 10210, Thailand

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 05期

关键词：

cyclization; ketones; naphthols; negundin A; silver; ENANTIOSELECTIVE SYNTHESIS; BINOL LIGANDS; 2-NAPHTHOLS; DERIVATIVES; ALKYNES; NAPHTHALENES; CYCLIZATION; INHIBITOR; COMPLEXES; PHOSPHINE;

D O I：

10.1002/ajoc.201800025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequential synthesis of beta-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 beta-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.

引用

页码：932 / 945

页数：14

共 2 条

[1] AgTFA-catalyzed ketonization and intramolecular aldol condensation of ortho-alkynylarylketones for the synthesis of β-naphthols and naphtho[2,3-B]furan-2(3H)-one: Toward the synthesis of negundin A
Nimnual, Phongprapan
Norseeda, Krissada
Akkachairin, Bhornrawin
Tummatorn, Jumreang
Laohapaisan, Pavitra
Supantanapong, Nantamon
Chuangsoongnern, Pennapa
Thongsornkleeb, Charnsak
Ruchirawat, Somsak
Sittihan, Satapanawat
Rodphon, Warabhorn
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[2] Enantioselective Total Synthesis of Cannogenol-3-O-α-L-rhamnoside via Sequential Cu(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions
Bhattarai, Bijay
Nagorny, Pavel
[J]. ORGANIC LETTERS, 2018, 20 (01) : 154 - 157

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