78469-77-9Relevant academic research and scientific papers
Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth
Huang, Yuahn-Sieh,Shih, Jing-Feng,Tsai, Yow-Fu,Wu, Yu-Fa
supporting information, p. 7491 - 7495 (2020/10/09)
A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.
Stereoselective Synthesis of C1–C7 and C6–C22 Fragments of Phostriecin, Goniothalamines, and Their Analogues
Purushotham Reddy,Vasudeva Reddy,Sabitha, Gowravaram
, p. 4389 - 4399 (2018/09/11)
The stereoselective synthesis of two fragments (C1–C7 and C6–C22) of the anti-tumor agent phostriecin has been achieved. The chiral hydroxy-vinyl-δ-lactone building block (fragment C1–C7) was subsequently utilized for the synthesis of 5-hydroxygoniothalamin, 5-acetoxygoniothalamin, and their derivatives.
Stereoselective Synthesis of the C27-C35 Eribulin Fragment and Its Utilization in Building Structurally Diverse Macrocycles
Konda, Saidulu,Khatravath, Mahender,Mallurwar, Naveen Kumar,Rao, Pallavi,Sripelly, Shivashankar,Iqbal, Javed,Arya, Prabhat
, p. 1663 - 1683 (2016/05/24)
A practical and scalable stereoselective synthesis of the western substituted tetrahydrofuran ring C27-C35 fragment of eribulin was developed by using (2S,3S)-tartaric acid as a cheap starting material that was converted into an intermediate through a stereoselective vinylation and cross-metathesis as the key steps. A regio-and stero-selective intramolecular oxy-Michael cyclization or an iodocyclization reaction finally provided the required western tetrahydrofuran ring fragment and its related isomeric analogues. These key fragments were further utilized in obtaining several types of macrocyclic derivatives for exploration of their biological properties. The simplicity of our present approach has the potential to be considered for large-scale syntheses of key fragments of eribulin and related analogues.
Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment
McNulty, James,McLeod, David,Jenkins, Hilary A.
supporting information, p. 688 - 692 (2017/01/18)
A total synthesis of the proposed structure of the natural macrolactone phomolide G (1) by a bidirectional strategy from L-tartaric acid is reported. The ω-terminus of the molecule was elaborated by nitrile extension, C3-alkylation and a substrate-controlled 1,3-ketone reduction. The α-terminus was extended by a C2aldehyde-to-alkenal homologation followed by an auxiliary controlled aldol reaction. Macrolactonization and deprotection yielded compound 1 (confirmed by X-ray analysis). This putative structure of phomolide G displayed discordant NMR spectroscopic data in comparison with those of the natural product. Detailed inspection of all NMR spectroscopic data available indicated phomolide G to be likely a diastereomer of 1. The synthetic strategy developed allows control of the absolute stereochemistry at all four chiral secondary alcohol groups. Further manipulation allowed for the preparation of diastereomer 33, the1H and13C NMR spectroscopic data of which are in full accord with that reported for the natural product.
A facile approach for the synthesis of C13-C24 fragments of maltepolides A, C and D
Rao, P. Sankara,Srihari
, p. 9629 - 9638 (2016/10/22)
A linear, chiron approach for the synthesis of C13-C24 fragments of cytostatic maltepolides A, C and D consisting of a tetrahydrofuran subunit and a chiral alkenyl/alkyl substituent is achieved from (+)-diethyl l-tartrate. The other chiral stereocenters were generated by employing key reactions such as Crimmins aldol, alkynylation and CeCl3·7H2O mediated Luche reduction reactions.
Stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core of (+)-muconin via Prins cyclization
Yadav,Reddy, U.V. Subba,Reddy, B.V. Subba
, p. 3860 - 3863 (2014/07/08)
A stereoselective synthesis of tetrahydropyran-tetrahydrofuran (THP-THF) core 2 of (+)-muconin (1) has been achieved using Prins cyclization as a key step to construct tetrahydropyran moiety. Other important transformations such as Wittig olefination, Sharpless epoxidation, regio-, and stereoselective exo-cyclization of the epoxy alcohol, titanocene induced regioselective deoxygenation of 2,3-epoxy alcohol, Grignard reaction, and Barton-McCombie reaction are successfully employed to accomplish the synthesis of THP-THF core 2.
Synthesis and protein kinase C (PKC)-C1 domain binding properties of diacyltetrol based anionic lipids
Mamidi, Narsimha,Panda, Subhankar,Borah, Rituparna,Manna, Debasis
, p. 3002 - 3013 (2015/01/08)
The protein kinase C (PKC) family of lipid-activated kinases plays a significant role in the regulation of diverse cellular functions including tumor promotion, apoptosis, differentiation, and others. The lipophilic second messenger diacylglycerols (DAGs) act as endogenous ligands for the PKCs in the presence of anionic phospholipids. To develop effective PKC regulators and understand the importance of anionic phospholipids in DAG binding of PKC isoforms, we conveniently synthesized octanoic acid containing diacyltetrol (DAT) based hybrid lipids with both DAG and anionic phospholipid headgroups within the same molecule. We also used palmitic and oleic acid containing hybrid lipids for additional understanding of the PKC-C1 domain binding mechanism. Biophysical studies showed that hydrophobic side chains, DAG and anionic phospholipids headgroups are necessary for their interaction with the C1-domain of PKC isoforms. The hybrid lipids DAT-PS and DAT-PA specifically interact with the PKCδ-C1b and PKCθ-C1b subdomains and showed 5- and 2.5-fold stronger binding affinity compared with DAG, respectively. Whereas, the PKCα-C1a subdomain interacts with the hybrid lipids, without any significant specificity. The present results show that hybrid lipids bind to the PKC C1b/a subdomains and can be further studied to decipher their binding mechanism and biological activities. This study proposes a new concept of developing PKC activators by using tetrol-based anionic hybrid lipids having both phospholipids and diacylglycerol headgroups within the same molecule. This study also supplies useful information for the binding potencies of hybrid lipids with PKC-C1 domains. This journal is
Total syntheses of d-allo-1-deoxynojirimycin and l-talo-1-deoxynojirimycin via reductive cyclization
Chavan, Subhash P.,Dumare, Nilesh B.,Pawar, Kailash P.
, p. 40852 - 40858 (2015/02/05)
Synthesis of a polyhydroxypiperidine framework for l-talo-1-deoxynojirimycin and d-allo-1-deoxynojirimycin was achieved from l-tartaric acid by employing flash dihydroxylation and reductive lactamisation as the key steps. This journal is
A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O
Vamshikrishna, Kuchena,Srinu, Garlapati,Srihari, Pabbaraja
, p. 203 - 211 (2014/03/21)
A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from l-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules.
Synthesis of the revised structure of acortatarin A
Geng, Hui Min,Stubbing, Louise A.,Li-Yang Chen, Jack,Furkert, Daniel P.,Brimble, Margaret A.
, p. 6227 - 6241 (2015/03/30)
A novel Maillard-type condensation between a primary amine derived from D-mannitol and a dihydropyranone, was used as a key step to access the unusual morpholine-spiroketal acortatarin A. The synthetic approach also enabled access to a C-2 analogue of acortatarin A, and can be used for the synthesis of related 2-formylpyrrole natural products.
