- C28Terpenoids from Lamiaceous Plant Perovskia scrophulariifolia: Their Structures and Anti-neuroinflammatory Activity
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Structurally unique C28 terpenoids, perovsfolins A (1) and B (2), were isolated from the aerial parts of an Uzbek medicinal plant, Perovskia scrophulariifolia (Lamiaceae). Their chemical structures including an unprecedented 6/8/6/6/6 pentacyclic carbon skeleton with a C6-C3 ester moiety were elucidated on the basis of spectroscopic analyses aided by density functional theory calculations as well as chemical evidence. Perovsfolin B (2) exhibited an anti-neuroinflammatory activity.
- Itoh, Kohji,Kajihara, Seita,Kashiwada, Yoshiki,Mamadalieva, Nilufar Z.,Niwa, Kanji,Tanaka, Naonobu,Tsuji, Daisuke
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p. 7667 - 7670
(2020/10/09)
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- Phlenumdines A?C, New lycopodium alkaloids isolated from phlegmariurus nummulariifolius
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Three new lycopodine-type alkaloids, phlenumdines A?C (1?3), have been isolated from the clubmoss Phlegmariurus nummulariifolius (Blume) Ching, and their structures were elucidated on the basis of spectroscopic data.
- Nakayama, Waka,Monthakantirat, Orawan,Fujikawa, Kazumi,Watthana, Santi,Kitanaka, Susumu,Makino, Toshiaki,Ishiuchi, Kanichiro
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p. 2247 - 2261
(2017/12/12)
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- The asymmetric total synthesis of (+)-salvianolic acid A
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An asymmetric synthesis of (+)-salvianolic acid A with cardioprotective properties, has been accomplished in a convergent manner in eight steps and 10.6% overall yield. This synthesis features an asymmetric addition of organometallics to optically pure 2,3-epoxypropionate in the presence of BF3·Et2O, Ru(III)-catalyzed directed [Formula presented] olefination, and I2-catalyzed isomerization reaction.
- Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang
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supporting information
p. 5047 - 5050
(2016/07/25)
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- Stereoselective α-Hydroxylation of Amides Using Oppolzer's Sultam as Chiral Auxiliary
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An Oppolzer's sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline products and the recyclability of the chiral auxiliary illustrate the practicability and scalability of the current approach.
- Zhang, Lumin,Zhu, Lili,Yang, Jun,Luo, Jisheng,Hong, Ran
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p. 3890 - 3900
(2016/05/24)
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- Asymmetric transfer hydrogenation of α-azido acrylates
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The asymmetric transfer hydrogenation of α-azido acrylates has been explored, a range of α-hydroxy esters are produced with good enantioselectivities (80-90% ee). The reaction was conducted in the wet HCO2H/NEt3 with Ru-TsDPEN A.
- Ji, Yang,Xue, Ping,Ma, Dan-Dan,Li, Xue-Qiang,Gu, Peiming,Li, Rui
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supporting information
p. 192 - 194
(2015/02/05)
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- Total synthesis of (+)-pentamethylsalvianolic acid C
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The total synthesis of a methylated analogue of (+)-Salvianolic acid C has been achieved. Key aspects of the synthetic route include an economical Cu(i) acetylide coupling, unique carboxyl activation conditions via microwave irradiation and a novel lipase catalysed kinetic resolution of a racemic mixture of secondary alcohol Danshensu. The preparation of this methylated analogue will not only improve the bioavailability, but also enable access to new and wider bioactivity applications for (+)-Salvianolic acid C.
- Alford, Benjamin L.,Huegel, Helmut M.
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supporting information
p. 2724 - 2727
(2013/06/04)
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- Synthesis of derivatives of methyl rosmarinate and their inhibitory activities against matrix metalloproteinase-1 (MMP-1)
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A series of MMP-1 inhibitors have been identified based upon a methyl rosmarinate scaffold using structure-based drug design methods. The best compound in the series showed an IC50 value of 0.4 μM. A docking study was conducted for compound (S)
- Yuan, Hu,Lu, Weiqiang,Wang, Liyan,Shan, Lei,Li, Honglin,Huang, Jin,Sun, Qingyan,Zhang, Weidong
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p. 148 - 157
(2013/05/09)
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- Enantioselective total synthesis of (+)-lithospermic acid
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An enantioselective synthesis of (+)-lithospermic acid, a potent anti-HIV agent, has been accomplished in a convergent manner in nine steps. The synthesis features an enantioselective intramolecular oxa-Michael addition catalyzed by a quinidine derivative
- Ghosh, Arun K.,Cheng, Xu,Zhou, Bing
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p. 5046 - 5049,4
(2012/12/12)
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- Enantioselective total synthesis of (+)-lithospermic acid
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An enantioselective synthesis of (+)-lithospermic acid, a potent anti-HIV agent, has been accomplished in a convergent manner in nine steps. The synthesis features an enantioselective intramolecular oxa-Michael addition catalyzed by a quinidine derivative
- Ghosh, Arun K.,Cheng, Xu,Zhou, Bing
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p. 5046 - 5049
(2013/01/15)
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- Synthesis of anti-HIV lithospermic acid by two diverse strategies
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An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation to generate an appropriately substituted benzo[b]furan ester followed by a stereoselective reduction of a carbon-carbon double bond with Mg-HgCl 2-MeOH. The second strategy relied on an aldol condensation between a suitably substituted methyl arylacetate and 3,4-dimethoxybenzaldehyde, followed by cyclization. Finally, a total synthesis of (+)-lithospermic acid was completed via coupling of a trans-dihydrobenzo[b]furan cinnamic acid with an enantiomerically pure methyl lactate.
- Varadaraju, Tirumala G.,Hwu, Jih Ru
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experimental part
p. 5456 - 5465
(2012/08/08)
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- A concise route to dihydrobenzo[b]furans: Formal total synthesis of (+)-lithospermic acid
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A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan- 3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
- Fischer, Joshua,Savage, G. Paul,Coster, Mark J.
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p. 3376 - 3379
(2011/09/12)
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- Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation
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The total synthesis of (+)-lithospermic acid is described. The efficient synthesis features an asymmetric alkylation via C-H bond activation to assemble the dihydrobenzofuran core of the natural product. This was accomplished via a chiral imine-directed C
- O'Malley, Steven J.,Tan, Kian L.,Watzke, Anja,Bergman, Robert G.,Ellman, Jonathan A.
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p. 13496 - 13497
(2007/10/03)
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- Chemocontrolled reduction of aromatic α-ketoesters by NaBH4: Selective synthesis of α-hydroxy esters or 1,2-diols
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α-Hydroxyesters 5a-g or diols 6a-g have been obtained in high yields by reduction of aromatic α-ketoesters 4 once or twice respectively by using NaBH4 as the reducer under suitable conditions. The use of a solvent that does not interact with the reagent allowed the double reduction to occur with only a slight excess of borohydride in very mild conditions.
- Dalla, Vincent,Cotelle, Philippe,Catteau, Jean Pierre
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p. 1577 - 1580
(2007/10/03)
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- Tricyclic CNS active agents by intramolecular Oxa-Pictet-Spengler reaction
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Mitsunobu inversion of the (S)-configurated lactate (S)-7, which is prepared in four steps starting from (S)-tyrosine, leads to the (R)-configurated lactate (R)-7. The key step in the transformation of the enantiomeric lactates (S)-7 and (R)-7 into the benzomorphan analogous tricycles (R,S)-16a,b, (S,R)-16a,b, (S,S)-22, and (R,R)-22 is an intramolecular Oxa-Rictet-Spengler reaction: The amides (S)-13, (R)-13, (S)-19 and (R)-19, in which the carbonyl moiety - masked as an acetal - is linked to the 2-phenylethanol moiety, are cyclized to give the tricyclic amides (R,S)-15, (S,R)-15, (S,S)-21, and (R,R)-21, respectively. In a concentration of 100 μM both enantiomers of 16a, 16b, and 22 are not able to compete with 3H-(+)-MK 801 for the phencyclidine binding sites of NMDA receptors. In vivo, only (R,S)-16b and (S,S)-22 exhibit weak sedative and analgesic activity.
- Wunsch,Zott,Hofner,Bauschke
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p. 487 - 495
(2007/10/02)
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- Melitric acids A and B, new trimeric caffeic acid derivatives from Melissa officinalis
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Two new polyphenolic compounds, melitric acids A (2) and B (5), were isolated from the aboveground part of Melissa officinalis (Labiatae) and their structures, consisting of three caffeic acid units, were determined from chemical reactions and spectral data. Rosmarinic acid (1) was also isolated.
- Agata,Kusakabe,Hatano,Nishibe,Okuda
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p. 1608 - 1611
(2007/10/02)
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- TWO CAFFEIC ACID TETRAMERS HAVING ENANTIOMERIC PHENYLDIHYDRONAPHTHALENE MOIETIES FROM MACROTOMIA EUCHROMA
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Two caffeic acid tetramers were isolated from the dried root of Macrotomia euchroma, and the structures were established on the basis of spectral data and chemical conversion.These two compounds are shown to have enantiomeric 1,2-dihydro-1-(3',4'-dihydrox
- Nishizawa, Makoto,Tsuda, Masashi,Hayashi, Koji
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p. 2645 - 2649
(2007/10/02)
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- The first isolation of lignans, megacerotonic acid and anthocerotonic acid, from non-vascular plants, Anthocerotae (Hornworts)
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The new lignans, megacerotonic acid and anthocerotonic acid, were isolated from the Anthocerotae (Hornworts), Megaceros flagellaris and Anthoceros punctatus. Their structures were determined by spectroscopic mothods. This is the first known example of lignans isolated from non-vascular plants.
- Takeda,Hasegawa,Shinizaki
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p. 4159 - 4162
(2007/10/02)
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