120019-27-4

Upstream product

• 124868-05-9 (2S,3R,4S,5S)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran 
• 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 
• 124868-07-1 (2S,3R,4S,5R)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 302348-88-5 (5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one 
• 359435-63-5 (5S)-5-hydroxy-(6S)-6-cis-styryl-5,6-dihydro-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 
• 1578-26-3 1-(2'-furyl)-2-trimethylsilanylethan-1-ol 
• 61243-05-8 (S)-1-(α-furyl)-1,2-ethanediol 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 115997-88-1 (2S,3S,4E)-1,3-O-benzylidene-2-O-benzoyl-5-phenyl-4-pentene-1,2,3-triol 

Downstream Products

• 65408-91-5 goniothalenol 
• 119850-44-1 (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl propionate 
• 359435-66-8 Z-(C-phenyl 5,6-dideoxy-2-O-trifluoromethanesulphonyl-α-L-lyxo-heptofuranosi)uro-5-eno-3,7-lactone 

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.

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.

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.

Enantioselective syntheses of isoaltholactone, 3-epi-altholactone, and 5-hydroxygoniothalamin

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

Enantiospecific Synthesis of (+)-Altholactone and its Three Stereoisomers

(+)-Altholactone 1 and (+)-7-epi-altholactone 3 were constructed from D-gulonolactone whereas their respective enantiomers (-)-altholactone 2 and (-)-7-epi-altholactone 4 were synthesized from D-mannose, involving stereocontrolled reduction of the lactols 21 as a key step.