118629-75-7Relevant academic research and scientific papers
The stereoselective total synthesis of (+)-8-ethylnorlobelol from anti-1,3-aminoalcohols
Reddy, B.V. Subba,Reddy, B. Phaneendra,Sivaramakrishna Reddy,Reddy, Y. Jayasudhan,Yadav
, p. 4960 - 4962 (2013)
A novel and efficient approach has been developed for the total synthesis of (+)-8-ethylnorlobelol (1) in a highly stereoselective manner. The key anti-1,3-aminoalcohol core is constructed through the reductive opening of 2-iodomethyl-4-amidotetrahydropyranyl ether which is prepared by a Prins/Ritter amidation sequence.
Total synthesis of diplodialides C and D
Ramanujan, Vyasabhattar,Kumar, Chebolu Naga Sesha Sai Pavan
, p. 332 - 340 (2018)
A highly convergent, stereoselective total synthesis of diplodialides C and D is described. The protocol involves the use of regioselective ring opening of a chiral epoxide, sequential double alkylation of 1,3-dithiane with a bromide and a chiral epoxide,
Total synthesis of anticancer agent EBC-23
Reddy, Dodda Vasudeva,Sabitha, Gowravaram,Rao, Tadikamalla Prabhakar,Yadav, Jhillu Singh
, p. 4202 - 4205 (2016)
Total synthesis of spiroketal EBC-23 has been described by two divergent approaches from three simple building blocks. Gold-catalyzed cycloisomerization of alkynol and acid-mediated spirocyclization of diketalketone were successfully utilized to effect spiroketal formation. A Cu(I)-P(Cy)3-catalyzed protocol for the highly regio- and stereocontrolled hydroboration of internal propargylic alcohol was effectively applied toward the β-hydroxy ketone via vinylboronates.
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence
Brun, Elodie,Bellosta, Véronique,Cossy, Janine
, p. 8668 - 8676 (2015/09/15)
The total synthesis of (+)-cryptocaryol A was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogeni
Diastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation-reductive cleavage sequence
Brun, Elodie,Bellosta, Véronique,Cossy, Janine
, p. 6718 - 6721 (2014/06/23)
Stereocontrolled and efficient access to all the diastereomers of 1,3,5,7-tetraol structural units was developed using a Prins cyclisation-reductive cleavage sequence applied to tetrahydropyran aldehydes. Furthermore, these tetraols can be selectively functionalized. This journal is the Partner Organisations 2014.
Stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids through prins-ritter reaction
Reddy, B.V. Subba,Ghanty, Supriya,Reddy, N. Siva Senkar,Reddy, Y. Jayasudhan,Yadav
, p. 1658 - 1663 (2014/06/09)
A stereoselective total synthesis of the 2-(2-hydroxyalkyl)piperidine alkaloids has been accomplished by a Prins-Ritter amidation sequence. Other steps involved in this synthesis are Jacobsen's hydrolytic kinetic resolution (HRK) and ring-closing metathes
Enantioselective total synthesis of a natural iridoid
Lee, Sujin,Paek, Seung-Mann,Yun, Hwayoung,Kim, Nam-Jung,Suh, Young-Ger
supporting information; experimental part, p. 3344 - 3347 (2011/09/12)
The first total synthesis of 6-hydroxy-7-(hydroxymethyl)-4- methylenehexahydrocyclopenta[c]pyran-1(3H)-one has been accomplished. A key feature of the synthesis includes facile construction of the bicyclic lactone intermediate via intramolecular Pd(0)-catalyzed allylic alkylation and the efficient transformation of this intermediate into the iridoid skeleton employing silicon tethered radical cyclization.
Stereospecific synthesis of a GS 4104 metabolite: Determination of absolute stereochemistry and influenza neuraminidase inhibitory activity
Lew, Willard,Escarpe, Paul A.,Mendel, Dirk B.,Sweeny, David J.,Kim, Choung U.
, p. 2811 - 2814 (2007/10/03)
The total synthesis for the determination of the absolute stereochemistry of a GS 4104 metabolite 3 is described. In addition, the influenza neuraminidase inhibitory activity of 3 and related intermediates are reported.
Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors
Kim, Choung U.,Lew, Willard,Williams, Matthew A.,Wu, Huiwei,Zhang, Lijun,Chen, Xiaowu,Escarpe, Paul A.,Mendel, Dirk B.,Laver, W. Graeme,Stevens, Raymond C.
, p. 2451 - 2460 (2007/10/03)
A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized and evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.
