147659-07-2Relevant articles and documents
Total syntheses of Prelactone V and Prelactone B
Raghavendra,Tadiparthi, Krishnaji,Yadav
, p. 17 - 19 (2017/03/15)
The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from D-glucose. The synthesis involves isopropylidene acetal formation of D-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.
Asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters
Peed, Jennifer,Perinan Dominguez, Ignacio,Davies, Iwan R.,Cheeseman, Matt,Taylor, James E.,Kociok-Koehn, Gabriele,Bull, Steven D.
supporting information; experimental part, p. 3592 - 3595 (2011/09/21)
A versatile methodology for the asymmetric synthesis of chiral δ-lactones containing multiple contiguous stereocenters has been developed that relies on a series of Evans' aldol, hydroxyl-directed cyclopropanation, methanolysis, and Hg(II) mediated cyclopropane ring-opening reactions for stereocontrol.
Total asymmetric syntheses of β-hydroxy-δ-lactones via umpolung with sulfur dioxide
Exner, Claudia J.,Laclef, Sylvain,Poli, Florent,Turks, Maris,Vogel, Pierre
supporting information; experimental part, p. 840 - 845 (2011/04/16)
Cyclic stereotriads and stereotetrads of the β-hydroxy-d-lactone type, e.g. prelactonesBandE, commonin polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy) penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-d-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The d-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3- dienes.
A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: Synthesis of (+)-prelactones B, C and V
Yadav,Reddy, M. Sridhar,Prasad
, p. 2133 - 2136 (2007/10/03)
Reactions of homoallylic alcohols with aldehydes in the presence of acid catalysts gave multisubstituted tetrahydropyrans with the creation of one to three new stereogenic centres in a single-pot process. The utility of this approach is extended to the en
A short and efficient synthesis of (+)-prelactone B
Dias, Luiz C.,Steil, Leonardo J.,Vasconcelos, Valeria De A.
, p. 147 - 150 (2007/10/03)
The asymmetric total synthesis of (+)-prelactone B, a biologically important natural β-hydroxy-δ-lactone derivative that contains a 2,3-trans-dialkylpyran ring system, is described. This approach involves the use of a very efficient oxazolidinone-mediated anti-aldol reaction, and a diastereoselective coupling between a ketene silyl acetal with an aldehyde followed by lactonization.
An efficient synthesis of (+)-prelactone B
Yadav,Reddy, K. Bhaskar,Sabitha
, p. 6475 - 6476 (2007/10/03)
An enantioselective synthesis of (+)-prelactone B 1 has been achieved on a multigram scale starting from a known bicyclic precursor 2. The key feature of the strategy is the generation of 3-stereogenic centres from a single bicyclic precursor, which has b
Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of β-hydroxy-δ-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B
Aggarwal, Varinder K.,Bae, Imhyuck,Lee, Hee-Yoon
, p. 9725 - 9733 (2007/10/03)
Catalytic and stoichiometric asymmetric sulfur ylide reactions were employed to prepare alkyl-aryl epoxide intermediates in a convergent manner. These epoxides were utilized in efficient syntheses of the mevinic acid analogue 1 and prelactone B. Graphical abstract.
Synthesis of (+)-prelactone B
Chakraborty, Tushar K.,Tapadar, Subhasish
, p. 2541 - 2543 (2007/10/03)
Radical-mediated opening of a trisubstituted epoxy alcohol using cp2TiCl was followed by diastereoselective reduction of the resulting product with a centrally located methylene group, flanked on both sides by two chiral hydroxyl-bearing carbon
Asymmetric Synthesis of 4,5-Disubstituted 3-Hydroxy δ-Lactones: Prelactone B and Prelactone V
Enders, Dieter,Haas, Mareile
, p. 2182 - 2184 (2007/10/03)
An efficient asymmetric synthesis of δ-lactones such as prelactone B has been developed. As key steps, the SAMP/RAMP-hydrazone methodology for the synthesis of 2-methylenated 1,3-diols and a homogenous hydrogenation were used.
Enantioselective Synthesis of γ,δ-Disubstituted β-Hydroxy δ-Lactones from Furans: Synthesis of (+)-Prelactone B and its C-4 Epimer
Csák?, Aurelio G.,Mba, Myriam,Plumet, Joaquín
, p. 2092 - 2094 (2007/10/03)
A new method for the enantioselective synthesis of γ,δ- disubstituted β-hydroxy δ-lactones (5,6-dialkyl-5,6-dihydropyran-2- ones) is reported and exemplified for (+)-prelactone B and its C-4 epimer. Our approach is based on the ring-enlargement of suitably functionalized optically pure 4-hydroxycyclopentanones, which are readily obtained from chiral 4-hydroxycyclopent-2-enones derived from furans. The procedure is amenable to the large-scale synthesis of the title compounds.
