85520-72-5Relevant academic research and scientific papers
Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
Allais, Christophe,Roush, William R.
supporting information, p. 2646 - 2649 (2017/05/24)
A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with (diisopinocampheyl)borane 4. This strategy was applied to the total synthesis of andrachcine 1, thus establishing with certainty the absolute and relative configuration of the natural product.
Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation
Punganuru, Surendra R.,Aviraboina, Sivaprasad,Srivenugopal, Kalkunte S.
, p. 375 - 378 (2016/07/06)
A concise stereoselective total synthesis of (+)-monocerin has been accomplished using cross metathesis, tandem dihydroxylation-SN2 cyclisation and intramolecular alkoxycarbonylation as key steps. Cross-metathesis of 2-iodo-3,4,5-trimethoxyvinylbenzene and (R)-hepten-4-ol, followed by tandem dihydroxylation-SN2 cyclisation generated a tri-substituted tetrahydrofuran ring. Finally, the dihydroisocoumarin was obtained by an intramolecular alkoxycarbonylation. In this paper, we have developed an expedient operationally simple Pd(OAc)2/bathocuproine catalysed alkoxycarbonylation under atmospheric pressure of carbon monoxide. The catalytic system developed here can be useful for the synthesis of various dihydroisocoumarins and phthalides.
Stereoselective total synthesis of the (Z)-isomer of a novel phytotoxic nonenolide from Phomopsis sp. HCCB03520 and its C-6 epimer
Reddy, Cheruku Ravindra,Das, Biswanath
, p. 67 - 69 (2014/01/06)
The (Z)-isomer of a phytotoxic nonenolide, (6S,7R,9R)-6,7-dihydroxy-9- propylnon-4-eno-9-lactone isolated from Phomopsis sp. HCCB03520 and its C-6 epimer have been synthesized through a common route starting from butyraldehyde. The synthesis involves enantioselective Maruoka allylation, Sharpless asymmetric epoxidation and intramolecular ring closing metathesis as the important steps.
The first stereoselective total synthesis of putaminoxin e and its epimer and evaluation of their biological properties
Sudhakar, Chithaluri,Reddy, Parigi Raghavendar,Kumar, Chityal Ganesh,Sujitha, Pombala,Das, Biswanath
experimental part, p. 1253 - 1258 (2012/04/10)
Putaminoxin E, a natural nonanolide, and its C-9 epimer were synthesized for the first time starting from pentane-1,5-diol and butyraldehyde. The synthetic sequences involve Maruoka asymmetric allylation, Sharpless kinetic resolution, and ring-closing metathesis as the key steps. The cytotoxic and antimicrobial activities of these compounds were evaluated. Putaminoxin E, a natural nonanolide, and its C-9 epimer were synthesized for the first time starting from pentane-1,5-diol and butyraldehyde. Copyright
Total synthesis of 2-(2-hydroxyalkyl)-piperidine alkaloids (-)-halosaline and (-)-8-epi-halosaline via iterative asymmetric allylation/RCM strategy
Krishna, Palakodety Radha,Reddy, Bonepally Karunakar,Srinivas, Palabindela
experimental part, p. 841 - 845 (2012/02/02)
Total synthesis of 2-(2-hydroxyalkyl)-piperidine alkaloids, (-)-halosaline and (-)-8-epi-halosaline is reported from n-butyraldehyde using iterative asymmetric allylation, nucleophilic substitution with an azide and ring-closing metathesis as the key reactions.
Novel synthesis of stagonolide-F, putaminoxin and aspinolide-A
Kamal, Ahmed,Reddy, Papagari Venkat,Balakrishna, Moku,Prabhakar, Singaraboina
, p. 143 - 149 (2013/01/10)
Novel synthesis of putaminoxin, stagonolide-F and aspinolide-A have been achieved by utilizing (S) and (R)- malic acid. The key feature of the synthetic strategy includes Horner-Wittig olefination, double bond reduction and Steglich esterification. Olefinic acid for putaminoxin and stagonolide-F was prepared from (S)-malic acid whereas olefinic acid for aspinolide-A was prepared from (R)-malic acid and olefinic alcohols for putaminoxin, stagonolide-F and aspinolide-A were prepared by using Brown's asymmetric allylboration.
Formal synthesis of (-)-Neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence
Martinez-Solorio, Dionicio,Jennings, Michael P.
experimental part, p. 4095 - 4104 (2010/09/11)
The formal synthesis of the unnatural (-)-neopeltolide core is discussed in detail. Efficient application of the Evans protocol for the synthesis of 1,3-syn-diols via an intramolecular hetero-Michael addition followed by reductive deprotection of the resulting benzylidene acetal allowed for swift access to the δ-lactone. Central to the synthetic approach is a tandem nucleophilic addition-diastereoselective axial reduction of an in situ generated oxocarbenium cation to assemble the β-C-glycoside moiety of the neopeltolide core.
The first total synthesis of putaminoxin and determination of its absolute configuration
Sabitha, Gowravaram,Yadagiri,Swapna,Yadav
scheme or table, p. 5417 - 5419 (2009/12/06)
Asymmetric synthesis of putaminoxin, a phytotoxic macrolide from the cultured dinoflagellate Amphidinium sp., has been accomplished. Absolute configuration of putaminoxin was concluded to be 1 from comparison of the NMR data and [α]D values of synthetic and natural putaminoxin.
Formal synthesis of herbarumin III
Gupta, Priti,Kumar, Pradeep
, p. 1688 - 1692 (2008/02/11)
An enantioselective synthesis of herbarumin III is described employing Jacobsen's hydrolytic kinetic resolution and Sharpless asymmetric dihydroxylation as the key steps.
A short enantioselective total synthesis of the phytotoxic lactone herbarumin III
Boruwa, Joshodeep,Gogoi, Naminita,Barua, Nabin C.
, p. 3521 - 3525 (2008/09/16)
The synthesis of the phytotoxic lactone herbarumin III in 11 % overall yield by fermentation of broth and mycelium of the fungus Phoma herbarum is described. Keck's asymmetric allylation and Sharpless epoxidation are applied to build the key fragment of the compound. A ring closing metathesis and esterification with 5-hexanoic acid are used to obtain the compound. The synthesis is initiated by the application of the catalytic asymmetric allyl protocol. Chain elongation of the aldehyde through Wittig olefination with triphenyl carbethoxymethyl phosphonium chloride supported on alumina under microwave irradiation provided the α, β - unsaturated ester as the major product. The ring opening metathesis with Grubbs second-generation catalyst gave Herbarumin III as a clear oil. The complete procedure involved the synthesis of the compound from n-butanal in 11 % overall yield.
