Isoaltholactone

3-Hy-droxy-2-phenyl-2,3,3a,7a-tetra-hydro-1H,5H-pyrano[3,2-b]pyrrol-5-one: crystal structure and Hirshfeld surface analysis.[Pubmed:28529789]

Acta Crystallogr E Crystallogr Commun. 2017 Apr 21;73(Pt 5):746-751.

The title Isoaltholactone derivative, C13H13NO3, has an NH group in place of the ether-O atom in the five-membered ring of the natural product. The five-membered ring is twisted about the N-C bond linking it to the six-membered ring, which has a half-chair conformation with the O atom connected to the ether-O atom lying above the plane defined by the remaining atoms. The dihedral angle between the mean planes of the rings comprising the fused-ring system is 75.10 (8) degrees . In the crystal, hy-droxy-O-Hcdots, three dots, centeredN(amine) hydrogen bonding sustains linear supra-molecular chains along the a axis. Chains are linked into a three-dimensional architecture via amine-N-Hcdots, three dots, centeredpi(phen-yl) and phenyl-C-Hcdots, three dots, centeredO(hy-droxy) inter-actions. The influence of the amine-N-Hcdots, three dots, centeredpi(phen-yl) contact on the mol-ecular packing is revealed by an analysis of the Hirshfeld surface.

Cobalt-catalyzed diastereoselective synthesis of C-furanosides. Total synthesis of (-)-isoaltholactone.[Pubmed:24127819]

J Org Chem. 2013 Dec 6;78(23):11807-14.

An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-Isoaltholactone.

Inhibitory effect of compounds from Goniothalamus tapis Miq. and Goniothalamus uvaroides King on platelet-activating factor receptor binding.[Pubmed:22002630]

Phytother Res. 2012 May;26(5):687-91.

Phytochemical investigation on the bark of Goniothalamus tapis Miq. and G. uvaroides King has resulted in the isolation of eight styryl-lactones, (-)-cryptomeridiol, liriodenine, 3-methyl-1H-benz[f]indole-4,9-dione, (-)-stigmasterol and dimethyl terephthalate. The structures of the compounds were elucidated by spectroscopic techniques. The compounds were evaluated for their effect on platelet-activating factor (PAF) receptor binding on rabbit platelets using (3) H-PAF as a ligand. Among the compounds tested, (-)-cryptomeridiol, (+)-goniothalamin and (+)-Isoaltholactone exhibited a significant and concentration-dependent inhibitory effect on PAF receptor binding, with inhibitory concentration (IC)(50) values of 17.5, 19.7 and 46.5 microm, respectively. The inhibitory effects of the first two compounds were comparable to that obtained from the positive control, cedrol. The results indicated that these compounds were strong PAF receptor binding inhibitors.

Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone.[Pubmed:21666896]

Chem Commun (Camb). 2011 Jul 21;47(27):7659-61.

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.

A convergent Pd-catalyzed asymmetric allylic alkylation of dl- and meso-divinylethylene carbonate: enantioselective synthesis of (+)-australine hydrochloride and formal synthesis of isoaltholactone.[Pubmed:17847148]

Chemistry. 2007;13(34):9547-60.

The use of a mixture of dl- and meso-divinylethylene carbonate as an electrophile in palladium-catalyzed asymmetric allylic alkylation reactions is reported. From the diastereomeric mixture of meso and chiral racemic starting materials, a single product is obtained in high optical purity employing either oxygen or nitrogen nucleophiles. The resulting dienes have proven to be versatile synthetic intermediates as each carbon is functionalized for further transformation and differentiated by virtue of the reaction. A mechanism for this intriguing transformation is proposed and a concise enantioselective total synthesis of (+)-australine hydrochloride is reported as well as a formal synthesis of Isoaltholactone.

Styryllactones from the rhizomes of Goniothalamus griffithii.[Pubmed:11254031]

J Asian Nat Prod Res. 1999;1(3):189-97.

Three new styryl-lactones 8-acetylgoniofufurone(1), 7-acetylgonio-pypyrone(3), and 5-acetylgoniopypyrone(4), along with ten known compounds, goniofufurone(2), goniopypyrone(5), goniothalamin, goniothalenol, (+)-Isoaltholactone, goniodiol, 7-acetylgoniodiol, goniotriol, 8-acetylgoniotriol, 9-deoxygoniopypyrone were isolated from the rhizomes of Goniothalamus griffithii Hook f. et. Thoms. Their structures were elucidated by IR, MS, NMR spectra and chemical evidence. All compounds showed cytotoxic activities against human cancer cell lines.

Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin.[Pubmed:10986088]

Org Lett. 2000 Sep 21;2(19):2983-6.

A flexible enantioselective route to highly functionalized alpha, beta-unsaturated delta-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, 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 alpha,beta-unsaturated delta-lactones via a short highly diastereoselective oxidation and reduction sequence.