124868-11-7Relevant articles and documents
Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone
Unsworth, William P.,Stevens, Kiri,Lamont, Scott G.,Robertson, Jeremy
supporting information; experimental part, p. 7659 - 7661 (2011/09/12)
We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.
Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone
Yadav, Jhillu Singh,Raju, Atcha Krishnam,Rao, Ponugoti Purushothama,Rajaiah, Gurram
, p. 3283 - 3290 (2007/10/03)
A flexible stereoselective route to synthesize both enantiomers of the highly functionalized substituted tetrahydrofurans and α,β- unsaturated-δ-lactones, goniothales diol, altholactone, and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulfonic acid.
A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone
Yadav,Rajaiah,Raju, A. Krishnam
, p. 5831 - 5833 (2007/10/03)
A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized α,β-unsaturated-δ-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid.
Enantioselective total synthesis of (+)-isoaltholactone
Peng, Xiaoshui,Li, Anpai,Lu, Jiangping,Wang, Qiaoling,Pan, Xinfu,Chan, Albert S.C
, p. 6799 - 6804 (2007/10/03)
A facile enantioselective route to highly functionalized α,β-unsaturated -δ-lactones has allowed for the synthesis of (+)-isoaltholactone in 6.4% overall yield from furylmethanol. This approach derived its asymmetry by applying Sharpless kinetic resolution on racemic 2-furylmethanol. The resulting pyranone was produced in high enantioexcess and was stereoselectively transformed into (+)-isoaltholactone via a highly diastereoselective epoxidation and a key PPTS catalyzed intramolecular cyclization.
An olefination approach to the enantioselective syntheses of several styryllactones
Harris, Joel M,O'Doherty, George A
, p. 5161 - 5171 (2007/10/03)
A flexible enantioselective route to highly functionalized α,β-unsaturated δ-lactones, has allowed for the syntheses of the styryllactones: altholactone, isoaltholactone, 3-epi-altholactone, 2-epi-altholactone and 5-hydroxy goniothalamin in 2.5, 10, 5, 1 and 13% overall yields from furfural, respectively. This approach derives its asymmetry by applying the Sharpless catalytic asymmetric dihydroxylation to vinylfuran. The resulting diols are produced in high enantioexcess and can be stereoselectively transformed into α,β-unsaturated-δ-lactones via a short highly diastereoselective oxidation and reduction sequence. Wittig olefination or Julia olefination reactions were used to introduce the phenyl group side chain either cis or trans selectively and these intermediates were further elaborated into the altholactone isomers via selective epoxidation reactions.
Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin
Harris, Joel M.,O'Doherty, George A.
, p. 2983 - 2986 (2007/10/03)
A flexible enantioselective route to highly functionalized γ,β-unsaturated δ-lactones has allowed for the syntheses of the styryllactones: isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin in 10%, 5%, and 13% overall yields from furfural, re
