Hauser-Kraus(以下简称H-K)是构建多取代对苯二酚及其衍生物的最有效方法之一。很多复杂天然产物的全合成都将H-K环化作为构建多环骨架的关键步骤(图1a)。1978年,Hauser课题组首次报道了以3-(苯磺酰基)酞和α,β-不饱和羰基化合物的[4+2]环化反应合成多取代对苯二酚。大约同一时间,Kraus课题组报道了3-氰基苯酞与...
Hauser-Kraus(以下简称H-K)是构建多取代对苯二酚及其衍生物的最有效方法之一。很多复杂天然产物的全合成都将H-K环化作为构建多环骨架的关键步骤(图1a)。1978年,Hauser课题组首次报道了以3-(苯磺酰基)酞和α,β-不饱和羰基化合物的[4+2]环化反应合成多取代对苯二酚。大约同一时间,Kraus课题组报道了3-氰基苯酞与...
Hauser-Kraus环化反应 碱性条件下,苯酞类化合物和α,β-不饱和羰基化合物立体选择性关环得到苯并氢醌的反应。加入氧化银氧化氢醌可以制备苯醌。 反应机理 反应实例 Hydroquinone (4). To LDA (3.3 mmol) in THF (4 mL) and HMPA at -78 ℃ was added 3-cyanophthalide 1 (3 mmol) in THF (3 mL) over...
Hauser–Kraus annulation of sulfonylphthalides with simple conjugated nitroalkenes follows the expected pathway to furnish naphthoquinones in moderate yields. However, a strategic variation of this reaction by employing nitroalkenes bearing an additional nucleophilic site results in [4+4] annulation leading ...
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Total synthesisHerein, we describe the first total synthesis of parvinaphthol B, a polyhydroxynaphthoate derived from the root of Pentas parvifolia which exhibits cytotoxic effects against the TNBC cell line. The key feature of the synthesis involves a Hauser-Kraus annulation to provide the poly...
ring closure reactions, annulation reactionsrearrangementsA Hauser—Kraus annulation of sulfonylphthalides with conjugated nitro alkenes furnishes naphthoquinones in moderate yields.doi:10.1002/chin.201648114Kumar, TarunSatam, NishikantNamboothiri, Irishi N. N.John Wiley & Sons, Ltd.Cheminform...
A formal total synthesis of nanaomycin D has been achieved. The strategy employed made use of a one-pot cyclisation–stereoselective reduction of a hydroxyketone to install the pyranonaphthalene moiety after execution of a Hauser–Kraus annulation using a chiral enone-lactone as the Michael acceptor...
Hauser–Kraus annulationA double Hauser–Kraus annulation between biscyanophthalide 4 and the d-mannose derived enone 39 provides access to an advanced intermediate 54 that is an excellent scaffold to effect an enantioselective total synthesis of crisamicin A 1....