147976-19-0Relevant academic research and scientific papers
The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction
Rehman, Mintu,Surendran, Sravya,Siddavatam, Nagendra,Rajendar, Goreti
, p. 329 - 333 (2022/01/20)
Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.
Two simple and alternative approaches for the synthesis of anticancer active goniothalamin
Narasimhulu, Manchala,Siva Prasad,Appa, Rama Moorthy,Lakshmidevi, Jangam,Venkateswarlu, Katta
, p. 326 - 337 (2018/07/05)
Two alternative and straightforward routes were developed for the construction of (R)-goniothalamin, a natural anticancer agent. The first method starts with (R)-glycidol involving stereoselective (partial) reduction of alkyne and sulfoxide Julia-Lythgoe
Diastereoselective Fluorocyclopropanation of Chiral Allylic Alcohols Using an α-Fluoroiodomethylzinc Carbenoid
Navuluri, Chandrasekhar,Charette, André B.
supporting information, p. 4288 - 4291 (2015/09/15)
Chiral fluorocyclopropyl carbinols were synthesized in high diastereoselectivities via a zinc mediated cyclopropanation reaction, using sec-allylic alcohols as simple building blocks. An enantioselective version of this transformation was achieved through
Total synthesis of a mevinic acid analog
Reddy, Thummalapally Srikanth,Reddy, Dorigondla Kumar,Narasimhulu, Manchala,Ramesh, Dasari,Venkateswarlu, Yenamandra
experimental part, p. 2158 - 2163 (2011/02/17)
Total synthesis of mevinic acid analog 1 has been achieved efficiently starting from chiral 2,3-O-isopropylidene-D-glyceraldehyde (2). The synthesis involves Mitsunobu reaction and Evans' intramolecular oxa-Michael syn-addition reactions as key steps. Cop
Synthesis of enantiomerically pure perhydrofuro[3,4-b]pyrans and perhydrofuro[3,4-b]furans
Tiecco, Marcello,Testaferri, Lorenzo,Bagnoli, Luana,Terlizzi, Raffaella,Temperini, Andrea,Marini, Francesca,Santi, Claudio,Scarponi, Catalina
, p. 1949 - 1955 (2007/10/03)
Olefinic diols, prepared from (R)-(+)-2,2-dimethyl-1,3-dioxolane-4- carboxaldehyde via olefination and hydrolysis, were converted into enantiomerically pure hydroxy substituted tetrahydrofuran derivatives by cyclization using N-phenylselenophthalimide and BF3. The PhSe group in the C-4 position of these tetrahydrofurans was then substituted by an allyl group using allyltributylstannane in the presence of AIBN. The selenium promoted cyclizations of the allyl tetrahydrofurans in which the OH and the allyl groups are trans to each other formed the enantiopure perhydrofuro[3,4-b]pyrans, while the cyclization of the allyl tetrahydrofurans in which the OH and the allyl groups are cis gave rise to the perhydrofuro[3,4-b]furans. These bicyclic products were finally deselenenylated with triphenyltin hydride and AIBN.
Stereoselective synthesis of the 1,N2-deoxyguanosine adducts of cinnamaldehyde. A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes
Rezaei, Mansoureh,Harris, Thomas M.,Rizzo, Carmelo J.
, p. 7513 - 7516 (2007/10/03)
α,β-Unsaturated aldehydes (enals) react with deoxyguanosine and have mutagenic potential. For higher enals, the reaction of deoxyguanosine gives diastereomeric 6-substituted 8-hydroxypyrimidopurinone products. These stereoisomers may have different local
