4693-91-8Relevant academic research and scientific papers
Total synthesis of two isoflavone C-glycosides (6-tert-butyl puerarin and 6-tert-butyl-4′-methoxypuerarin) through the deoxybenzoin pathway
Zou, Yunpeng,Zhang, Shouguo,Wen, Xiaoxue,wang, Gang,sun, Yunbo,Liu, Shuchen,Peng, Tao,Gao, Yue,Wang, Lin
, p. 2835 - 2837 (2017)
The total synthesis of two isoflavone C-glycosides (6-tert-butylpuerarin and 6-tert-butyl-4′-methoxypuerarin) was achieved through the deoxybenzoin pathway with overall yields of 14.6% and 14.2%. The key intermediate 12 was obtained by de-tert-butylation
An efficient total synthesis of a natural Penipanoid A
Basavaiah, K.,Rao, G. Nageswara,Reddy, A. Satyanarayana,Reddy, V. Krishna
, (2022/01/14)
Natural products with heterocyclic core units are ample and widespread in nature, with many compounds exhibiting promising therapeutic properties. Penipanoid A (1) is a triazole based natural product isolated from the marine sediment derived fungus Penici
R - alpha - amino -4 - methoxybenzene b amide synthesis method
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Page/Page column 5-8, (2019/03/28)
The invention relates to a preparing method of a compound, in particular to a compounding method of R-alpha-amino-4-anisyl phenyl acetamide, which comprises the following steps: acidylation, methylation and aminolysis. In the step of acidylation, raw mate
Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair
Cao, Weidi,Tan, Davin,Lee, Richmond,Tan, Choon-Hong
supporting information, p. 1952 - 1955 (2018/02/17)
Highly enantioselective bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary alcohols in high yields with excellent enantioselectivities (up to 95% ee). The isolation of an α-silylcarbinol intermediate as well as DFT calculations revealed that the 1,2-anionotropic rearrangement occurred via a bisguanidinium silicate ion pair, which is the stereodetermining step. The chiral center formed is then retained without inversion through the subsequent [1,2]-Brook rearrangement. Crotyl acylsilanes were smoothly transformed into homoallylic linear crotyl alcohols with retention of E/Z geometry, and no branched alcohols were detected. This clearly suggested that the 1,2-anionotropic rearrangement occurred through a three-membered instead of a five-membered transition state.
Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols
Chachignon, Hélène,Kondrashov, Evgeniy V.,Cahard, Dominique
supporting information, p. 965 - 971 (2018/01/27)
Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).
A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan
Yalamanchili, Chinni,Chittiboyina, Amar G.,Chandra Kumar Rotte, Sateesh,Katzenellenbogen, John A.,Helferich, William G.,Khan, Ikhlas A.
, p. 2020 - 2029 (2018/03/21)
For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.
Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group
Patel, Jignesh J.,Laars, Marju,Gan, Wei,Board, Johnathan,Kitching, Matthew O.,Snieckus, Victor
supporting information, p. 9425 - 9429 (2018/07/29)
A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.
Synthesis and peripheral substituent effects of bay-annulated indigo derivatives
Furuyama, Taniyuki,Tamura, Daichi,Maeda, Hajime,Segi, Masahito
, p. 2913 - 2916 (2018/06/25)
In this study, indolo-naphthyridine-6,13-diones (5a–d) with four different peripheral substituents were prepared via bay-annulation reactions of indigo. The resulting compounds (5a–d) exhibited fluorescence in the red to near-IR region, while the parent indigo molecule showed no fluorescence. Although the peripheral substituents were oriented to the exterior of the π-conjugated system, the electronic structure affected the absorption and fluorescence spectra. Moreover, calculated molecular orbitals and absorption spectra successfully reproduced the experimental absorption spectra and cyclic voltammograms.
Heterocyclic pyrrolizinone and indolizinones derived from natural lactam as potential antifungal agents
Wang, Shuangshuang,Bao, Longzhu,Wang, Wenda,Song, Di,Wang, Jingjing,Cao, Xiufang
, p. 257 - 266 (2018/08/04)
With the aim to develop highly potential active heterocyclic compounds, two series of multi-substituted pyrrolizinone and indolizinones derived from lactam were designed, synthesized and evaluated for their potential antifungal activities against six species of the plant pathogen fungi (Fusarium graminearum, Sclerotinia sclerotiorum, Phomopsis adianticola, Gloeosporium theae-sinensis, Alternaria tenuis Nees, Magnaporthe oryzae). The structure of all the newly molecules were confirmed by analytical spectroscopic data, including 1H NMR, 13C NMR and ESI-MS. According to the preliminary studies on bio-evaluation assay, some of the obtained compounds exhibited moderate and broad-spectrum activities against six fungi compared to the intermediates 6a, 6f and the hymexazol. Particularly, the inhibition rate of compounds 7l, 7m and 7t reached 69.25%, 74.76%, 65.38% against Phomopsis adianticola and Magnaporthe oryzae in vitro activity. Furthermore, compounds 7l and 7t displayed obviously inhibition activities against Phomopsis adianticola compared to the hymexazol. Consequently, compounds 7l and 7t with six-membered alkane ring could be used as new motifs for further investigation.
Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
supporting information, p. 12347 - 12351 (2018/09/10)
The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
