65408-91-5

Usage

Uses

Used in Pharmaceutical Industry:
Altholactone is used as an anticancer agent for its potential to inhibit the growth of cancer cells. Its antioxidant and anti-inflammatory properties also contribute to its potential use in reducing inflammation in the body.
Used in Antimicrobial Applications:
Altholactone is used as an antimicrobial agent due to its ability to combat harmful microorganisms, which can be beneficial in treating infections and promoting overall health.
Used in Antiviral Applications:
Altholactone is used as an antiviral agent for its potential to inhibit viral activities, which can be advantageous in managing viral infections and improving immune response.
Overall, altholactone's diverse range of potential applications highlights its importance as a bioactive compound with promising health benefits. Further research is necessary to explore its full potential and optimize its use in various industries.

InChI:InChI=1/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11+,12+,13+/m0/s1

Upstream product

• 65409-11-2 (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate 
• 359435-63-5 (5S)-5-hydroxy-(6S)-6-cis-styryl-5,6-dihydro-pyran-2-one 
• 359435-67-9 3-formyloxy-altholactone 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 302348-88-5 (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 
• 302348-81-8 (5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 
• 474126-25-5 3-acetyl-isoaltholactone 
• 607376-02-3 ethyl 2,2-dimethyl-6-phenyl-(3aS,4R,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxole-4-carboxylate 
• 129694-47-9 (2S,3R,6S)-6-(1-Ethoxyethoxy)-2-<(E)-styryl>-3,6-dihydro-2H-pyran-3-ol 
• 129694-46-8 (2S,6S)-6-(1-Ethoxyethoxy)-2-<(E)-styryl>-6H-pyran-3(2H)-one 
• 160699-77-4 (5S,6S)-5-hydroxy-6-[(E)-styryl]-5,6-dihydro-2H-pyran-2-one 
• 302348-75-0 (3S)-3-tert-butyldimethylsilanyloxy-6-oxo-3,6-dihydro-2H-pyran-(2S)-2-carbaldehyde 
• 222986-37-0 (S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol 
• 302348-87-4 (5S)-5-tert-butyldimethylsilanyloxy-(6S)-6-hydroxymethyl-5,6-dihydro-pyran-2-one 

Downstream Products

• 65408-91-5 (2S,3R)-3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one 
• 219949-41-4 6,7-dihydro-7-methoxy-altholactone 
• 199326-63-1 (-)-etharvensin 
• 158673-96-2 (2R,3R,3aS,7aS)-tetrahydro-3-hydroxy-2-phenyl-2H-furo[3,2-b]pyran-5(6H)-one 
• 65409-11-2 (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate 
• 446253-18-5 (R)-3-((2R,3S,4S,5R)-3,4-Dihydroxy-5-phenyl-tetrahydro-furan-2-yl)-3-methoxy-propionic acid methyl ester 
• 139626-38-3 (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one 

Relevant academic research and scientific papers

Synthesis of (+)-altholactone, (+)-7-epi-altholactone, (?)-etharvensin, and (+)-alumheptolide-A using Pd-catalyzed carbonylation

Syntheses of (+)-altholactone isolated from Goniothalamus giganteus and its C-7 epimer (+)-7-epi-altholactone, (?)-etharvensin and (+)-alumheptolide-A were achieved. The lactone ring of these compounds was constructed using Pd-catalyzed carbonylation.

The first total synthesis of (+)-goniothalesacetate and syntheses of (+)-altholactone, (+)-gonioheptolide A, and (-)-goniofupyrone by an asymmetric acetate aldol approach

The first stereoselective total synthesis of (+)-goniothalesacetate and total synthesis of several bioactive styryl lactones, (+)-altholactone, (+)-gonioheptolide A, and (-)-goniofupyrone have been achieved from an advanced intermediate, which can be derived from l-(+)-DET.

Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone

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.

Apoptotic activities in closely related styryllactone stereoisomers toward human tumor cell lines: Investigation of synergism of styryllactone-induced apoptosis with TRAIL

A related series of styryllactones with small functional and stereochemical variations were compiled for a comparative study of their apoptotic activities toward two tumorigenic and one non-tumorigenic control cell line. While a substantial range of intrinsic activity was observed, the relative order of activity of the different compounds toward the cell types varied somewhat as did the relative ratios of apoptosis and necrosis observed in conjunction with the loss of cell viability. While some of the styryllactones showed substantial activity, a small but significant apoptosis-induced synergism was demonstrated with (-)-altholactone and TRAIL (tumor necrosis factor-related apoptosis-inducing ligand).

Asymmetric synthesis of (+)-altholactone: A styryllactone isolated from various goniothalamus species

The asymmetric total synthesis of (+)-altholactone (1), a member of the styryllactone family of natural products displaying cytotoxic and antitumor activities, is described. Key steps include a RAMP-hydrazone a-alkylation (RAMP = (R)-1-amino-2-methoxymethylpyrrolidine) of 2,2-dimethyl-1,3-dioxan-5-one, a boron-mediated aldol reaction, a six- to five-membered ring acetonide shuffling, an oxidative 1,5-diol to δ-lactone conversion and a stereoselective ring-closure to generate the annulated tetrahydrofuran moiety with inversion of configuration.

Stereoselective synthesis of (+)-goniodiol, (+)-goniotriol, (-)-goniofupyrone, and (+)-altholactone using a catalytic asymmetric hetero-Diels-Alder/allylboration approach

The stereoselective total synthesis of several members of the styryllactone family was achieved efficiently from common intermediate 8, prepared by a catalytic asymmetric inverse-electron-demand hetero-Diels-Alder/allylboration sequence. The transformatio

Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone

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

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

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

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.