Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
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TLDR
In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.Abstract:
The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.read more
Citations
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Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (±)-Cephalotaxine.
TL;DR: A stereoselective N-iminium ion cyclization with allylsilane to construct vicinal quaternary-tertiary carbon centers to furnish the spiro-ring system is developed for the concise synthesis of (±)-cephalotaxine.
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A Versatile Solid Phase Synthesis of Lavendustin A and Certain Biologically Active Analogs
Rajesh Devraj,Mark Cushman +1 more
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Divergent Synthesis of Cytotoxic Styryl Lactones from d-Xylose. The First Total Synthesis of (+)-Crassalactone C
Velimir Popsavin,Goran Benedeković,Bojana Srećo,Mirjana Popsavin,Jovana Francuz,and Vesna Kojić,Gordana Bogdanović +6 more
TL;DR: In a preliminary bioassay, all three natural products 1, 2, and 3 showed remarkable in vitro antiproliferative activities against K562, Raji, and HeLa neoplastic cell lines.
Journal ArticleDOI
Benzylation of hydroxy groups with tertiary amine as a base
J.W. Gathirwa,Toshihide Maki +1 more
TL;DR: The benzylation of hydroxy groups in the presence of tertiary amines is described in this article, where a mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields.
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Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C
Shoji Kobayashi,Yusuke Takahashi,Kazuo Komano,Babak Alizadeh,Yuuya Kawada,Tohru Oishi,S. Tanaka,Yoshihiro Ogasawara,S. Sasaki,Masahiro Hirama +9 more
TL;DR: In this paper, the ABCDE ring moiety of ciguatoxin CTX3C was synthesized stereoselectively using a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation.
References
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Journal ArticleDOI
Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
Oyo Mitsunobu,Masaaki Yamada +1 more
TL;DR: In this article, the reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol has been studied.
Journal ArticleDOI
Synthesis of lactones and cycloalkanes. Cyclization of ω-hydroxy acids and ethyl α-cyano-ω-hydroxycarboxylates
Journal ArticleDOI
Stereoselective and Stereospecific Reactions. III. Benzoylation, Cyclfzation, and Epimerization of Diols
TL;DR: The benzoylation of various classes of diols by means of diethyl azodicarboxylate and triphenylphosphine was carried out at room temperature as mentioned in this paper.
Journal ArticleDOI
Reaktionen mit phosphororganischen Verbindungen. XLII. Nucleophile Substitutionen an Hydroxysteroiden mit Hilfe von Triphenylphosphan/Azodicarbonsäureester†‡
Hans Loibner,Erich Zbiral +1 more
TL;DR: Nucleophilic substitution reactions of Hydroxysteroids using Triphenylphosphane/diethylazodicarboxylate in benzene was described in this article, where it was not possible to run this substitution process in the hitherto used solvent THF.
Journal ArticleDOI
Eine neue Synthese von (±)-Pyrenophorin
TL;DR: The synthesis of pyrenophorin (I), a 16-membered dilactone metabolite of plant pathogenic fungi is described, which involves removal of the acetal groups and the addition of protected functional groups to the ethylene acetal.
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