144178-30-3Relevant academic research and scientific papers
Stereoselective total synthesis of diplodialide A
Ramakrishna, Kolluri,Sreenivasulu, Reddymasu,Rao, Mandava Venkata Basaveswara,Vidavalur, Siddaiah,Reddy, Boggu Jagan Mohan
, p. 931 - 937 (2021)
Abstract: An efficient stereoselective total synthesis of Diplodialide A has been achieved from inexpensive and commercially available starting material (R)-propylene oxide. This linear synthesis utilizes Wittig reaction, alkylation of 1,3-dithiane and Yamaguchi macrolactonization as key steps. Graphic abstract: [Figure not available: see fulltext.]
An alternative total synthesis of diplodialide-B
Kalavakuntla, Chiranjeevi,Kummari, Vijaya Babu,Yadav, Jhillu Singh
, p. 3324 - 3328 (2019)
In this paper, an enantioselective synthesis of diplodialide-B has been described. To accomplish this target, a combination of regioselective ring opening of the chiral epoxide, Jacobsen hydrolytic kinetic resolution and Yamaguchi macrolactonization were used as the key steps.
Determination of the Absolute Configuration of Gliomasolide D through Total Syntheses of the C-17 Epimers
Seetharamsingh,Ganesh, Routholla,Reddy, D. Srinivasa
, p. 560 - 564 (2017)
The absolute configuration at C-17, the carbon bearing the distal hydroxy group of the 14-membered natural product gliomasolide D, was assigned as R by comparison of 13C NMR shifts and specific rotation values of the epimers at C-17. The first
Total synthesis of the Z -isomers of the proposed and revised structures of aspergillide B via an iodocyclization and ring-closing metathesis strategy
Pradhan, Tapas R.,Das, Pragna P.,Mohapatra, Debendra K.
, p. 1177 - 1184 (2014)
The synthesis of Z-isomers of both the proposed and revised structures of aspergillide B is described. A divergent route is employed that involves kinetically controlled ring-closing metathesis for the construction of a 14-membered macrocyclic ring, ester formation under Yamaguchi conditions, a Wacker-type oxidative cyclization for creation of the C4 stereogenic center and a previously reported diastereoselective isomerization-iodocyclization strategy for the construction of the 2,6-trans-disubstituted tetrahydropyran subunit. Georg Thieme Verlag Stuttgart, New York.
Formation of macrocycles via ring-closing olefin metathesis
Choon Woo Lee,Grubbs
, p. 7155 - 7158 (2001)
The enhanced metathesis activity of 1,3-dimesityl-4,5-dihydroimidazole-2-ylidene ruthenium carbene catalyst 3 significantly increases the feasibility of synthesizing macrocyclic compounds. Catalyst 3 exhibits sufficient activity in RCM to dimerize α,β-unsaturated ester substrates and afford the corresponding head-to-tail (E,E)-dimeric (and trimeric) macrocycles. The dimerization appears to be under thermodynamic control with the product mixture dependent not only on the electronic and steric nature of the substrate but also on concentration.
Enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri
Zhou, Yun,Yang, Pengfei,Li, Shuoning,Wang, Lifeng,Yin, Jingwei,Zhong, Jiangchun,Dong, Yanhong,Liu, Shangzhong,Wang, Min,Bian, Qinghua
, p. 338 - 343 (2017)
The first enantioselective synthesis of (2R,13R,8Z)-2,13-diacetoxy-8-heptadecene 1, the major component of the sex pheromone of the pear leaf midge, Dasineura pyri, has been achieved. The key steps include the (R,R)-BINOL/Ti(OiPr)4catalyzed alkynylzinc addition to an unsaturated aldehyde, the ring-opening of the chiral epoxide with a Grignard reagent, and the partial reduction of an acetylenic diol ester to a (Z)-olefinic diol ester with hydrogen and P2-Ni.
Exploiting the reversibility of olefin metathesis. Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin.
Fuerstner,Thiel,Ackermann
, p. 449 - 451 (2001)
[figure: see text] The formation of the trisubstituted cycloalkene 7 by RCM of diene 5 proceeds via the acyclic dimer 6, thus demonstrating the ready reversibility of olefin metathesis if catalyzed by "second generation" ruthenium carbene complexes such as 2-4. When applied to acrylate 11, these catalysts trigger a cyclooligomerization process that evolves with time and serves as key step en route to the lactide antibiotic (-)-pyrenophorin 8.
Total synthesis and stereochemical revision of relgro and 10′-oxorelgro
Gaddam, Janardhan,Reddy, G. Sudhakar,Marumudi, Kanakaraju,Kunwar, Ajit C.,Yadav, Jhillu S.,Mohapatra, Debendra K.
, p. 5601 - 5614 (2019/06/13)
The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10′-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation and CD spectral data led to the revision of the absolute configuration at C-6′ for both relgro and 10′-oxorelgro. Moreover, the 1H as well as 13C NMR data are reported for the first time for relgro.
A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun
, p. 7227 - 7237 (2019/06/07)
A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu
A concise stereoselective total synthesis of (-)-cephalosporolide D
Alluraiah, Gurrala,Sreenivasulu, Reddymasu,Sadanandam, Palle,Anitha, Kowthalam,Raju, Rudraraju Ramesh
, p. 451 - 455 (2016/02/16)
A concise stereoselective total synthesis of eight-membered lactone (-)-cephalosporolide D has been derived from inexpensive and commercially available starting material (S)-propylene epoxide. This concise synthesis utilizes Grignard reaction, Noyori asym
