564-24-9Relevant academic research and scientific papers
Method for synthesizing beta-damascenone
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Paragraph 0048; 0051; 0052, (2019/01/14)
The invention discloses a method for synthesizing beta-damascenone. The method mainly comprises the following steps: oxidizing citral through sodium chlorite; carrying out catalytic cyclization through concentrated phosphoric acid to obtain alpha-cyclogeranic acid; eliminating the alkalinity of the alpha-cyclogeranic acid under the action of thionyl chloride to obtain cyclogeranenone; carrying outaddition on the cyclogeranenone and allylmagnesium chloride and carrying out acidic isomerization to obtain alpha-damascenone; carrying out epoxidation on the alpha-damascenon through peroxyacetic acid, and carrying out alkaline ring opening through potassium carbonate; catalytically heating and dehydrating through para-toluenesulfonic acid to obtain the beta-damascenone. The method disclosed bythe invention has the advantages that raw materials are cheap and easy to obtain, reaction conditions are moderate and the operation is simple and convenient; another useful spice alpha-damascenone can be synchronously synthesized and the method is a method which is suitable for industrial production of the beta-damascenone.
Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation
Nicolaou,Hale, Christopher R. H.,Nilewski, Christian,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Nilewski, Lizanne G.,Beabout, Kathryn,Wang, Tim T.,Shamoo, Yousif
supporting information, p. 12137 - 12160 (2014/11/08)
The details of the total synthesis of viridicatumtoxin B (1) are described. Initial synthetic strategies toward this intriguing tetracycline antibiotic resulted in the development of key alkylation and Lewis acid-mediated spirocyclization reactions to form the hindered EF spirojunction, as well as Michael-Dieckmann reactions to set the A and C rings. The use of an aromatic A-ring substrate, however, was found to be unsuitable for the introduction of the requisite hydroxyl groups at carbons 4a and 12a. Applying these previous tactics, we developed stepwise approaches to oxidize carbons 12a and 4a based on enol- and enolate-based oxidations, respectively, the latter of which was accomplished after systematic investigations that revealed critical reactivity patterns. The herein described synthetic strategy resulted in the total synthesis of viridicatumtoxin B (1), which, in turn, formed the basis for the revision of its originally assigned structure. The developed chemistry facilitated the synthesis of a series of viridicatumtoxin analogues, which were evaluated against Gram-positive and Gram-negative bacterial strains, including drug-resistant pathogens, revealing the first structure-activity relationships within this structural type.
Total synthesis and structural revision of viridicatumtoxin B
Nicolaou,Nilewski, Christian,Hale, Christopher R. H.,Ioannidou, Heraklidia A.,Elmarrouni, Abdelatif,Koch, Lizanne G.
supporting information, p. 8736 - 8741 (2013/09/12)
Will the real viridicatumtoxin B please stand up: The total synthesis of viridicatumtoxin B resulted in its structural revision and opens the way for analogue construction and biological evaluation of this complex tetracycline-like antibiotic. The highly convergent strategy employed allows for swift construction of the entire carbocyclic framework of the molecule. Copyright
Synthesis of the spirochroman core of dihypoestoxide and stereochemical proposal for the natural product
Uroos, Maliha,Hayes, Christopher J.
scheme or table, p. 5294 - 5297 (2011/02/22)
The tricyclic spirochroman core of dihypoestoxide has been synthesized from geranoic acid in seven steps using a hetero-Diels-Alder cycloaddition as a key step, thus providing support for the proposed biosynthesis of the natural product. Furthermore, analysis of the 13C NMR data obtained for all four diastereoisomers of the synthetic spirochroman core has allowed us to propose a full stereochemical assignment for dihypoestoxide.
Improved synthesis of methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1- carboxylate, an A-ring intermediate for (±)strigol
Qianchao,Shiqing, Pi,Xinzhi, Chen
, p. 494 - 496 (2008/09/21)
Methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate was synthesised over eight steps from the starting material of citral instead of α-ionone. KMnO4, HC(OEt)3 and O2/TEMPO/CuCl were substituted for NaIO4, CH3I and pyridinium chlorochromate, respectively. Every step was simplified and gave a 48% overall yield. The procedure is suitable for large scale production.
NOVEL CYCLOHEXENE CARBOAMIDES AND CARBOTHIOAMIDES
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Page/Page column 10-11, (2008/06/13)
A compound or a mixture of compounds comprising an aromachemical compound of the formula (I): wherein: formula (II), is formula (III), or formula (IV); R is a straight or branched chain, saturated or unsaturated hydrocarbyl group; preferably, alkyl or alkenyl, having l-8 carbon atoms; R1 is a straight or branched chain, saturated or unsaturated hydrocarbyl group; preferably, alkyl or alkenyl, having l-8 carbon atoms; x is an integer from l to 8; y is an integer from 0 to 4, and Z is 0 or S, as well as compositions, products, preparations or articles having improved aroma, fragrance or odor characteristics containing as active ingredient such compound or mixture of compounds.
Isolation, synthesis, and anti-tumor activities of a novel class of podocarpic diterpenes
Xiong, Yi,Wang, Kuiwu,Pan, Yuanjiang,Sun, Hongxiang,Tu, Jue
, p. 786 - 789 (2007/10/03)
A novel unusual 17-carbon diterpenoid, named (+)-7-deoxynimbidiol, was isolated from the stalks of Celastrus hypoleucus (Oliv.) Warb. Its racemate and derivatives were synthesized, and the inhibitory activities of these compounds against four cultured human-tumor cell lines were evaluated. The structure-activity relationship was discussed.
Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether
Gan, Yonghong,Li, Anpai,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei
, p. 781 - 787 (2007/10/03)
A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-α-cyclocitral. Copyright (C) 2000 Elsevier Science Ltd.
Stereoselective synthesis of (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether
Yonghong, Gan,Xinfu, Pan
, p. 130 - 132 (2007/10/03)
A facile stereoselective synthetic procedure to (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether has been developed with high stereoselectivity and overall yield.
