96422-52-5

Usage

Uses

Used in Organic Synthesis:
(6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one is used as a building block in organic synthesis for its unique structure and properties, enabling the production of complex molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one is utilized as a key intermediate for the synthesis of pharmaceuticals, owing to its potential biological activities and chiral center.
Used in Pharmaceutical Development:
(6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one is employed in pharmaceutical development as a target for research and development due to its potential applications in medicine.

InChI:InChI=1/C13H14O4/c14-11-8-4-7-10(17-11)13(16)12(15)9-5-2-1-3-6-9/h1-6,8,10,12-13,15-16H,7H2/t10-,12-,13+/m1/s1

Upstream product

• 163630-06-6 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one 
• 859520-59-5 (4S,5R)-4-((2R,6S)-6-Ethoxy-5,6-dihydro-2H-pyran-2-yl)-5-phenyl-[1,3]dioxolan-2-one 
• 100-52-7 benzaldehyde 
• 474958-70-8 (1S,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenyl-but-3-en-1-ol 
• 474958-72-0 (1R,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenylbut-3-en-1-ol 
• 474958-71-9 (1R,2S)-2-(methoxyethoxymethoxy)-1-phenylbut-3-enyl 4-nitrobenzoate 
• 80541-30-6 (1S,2R)-1-(2-furyl)-2,3-(dimethylmethylen-dioxy)-1-propanol 
• 153000-32-9 (R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one 
• 1256338-98-3 methyl (Z)-(5R,6S,7R)-7-(tert-butyldimethylsiloxy)-5,6-(isopropylidenedioxy)-7-phenylhept-2-enoate 
• 1261161-28-7 (R)-6-((1S,2R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxy-2-phenylethyl)-5,6-dihydropyran-2-one 
• 181534-66-7 (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one 
• 181534-68-9 (5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one 
• 214678-54-3 3-Benzenesulfonyl-4-{(4R,5S)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester 
• 221639-49-2 (5S,6R)-5-acetoxy-6-<(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-5,6-dihydro-2H-pyran-2-one 

Downstream Products

• 194355-08-3 4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester 
• 96422-53-6 (6R,7R,8R)-goniodiol-7-monoacetate 
• 144429-71-0 (6R,7R,8R)-goniodiol-8-monoacetate 
• 194355-09-4 (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one 
• 194355-10-7 (-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one 
• 136685-37-5 (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one 
• 136778-40-0 7,8-di-O-acetyl-goniodiol 

Relevant academic research and scientific papers

Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e

A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.

A concise enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol via Co-catalyzed HKR of anti-(2SR, 3RS)-3-methoxy-3- phenyl-1, 2-epoxypropane

A short, enantioselective synthesis of (+)-goniodiol and (+)-8-methoxygoniodiol, cytotoxic styryllactones, has been achieved in high optical purities (99% ee). The strategy employs Co-catalyzed HKR of racemic anti-(2SR, 3RS)-3-methoxy-3-phenyl-1, 2-epoxypropane and Lewis acid-mediated diastereoselective allylation of aldehyde as chiral inducing key reactions.

Tandem α-aminoxylation-allylation reaction based approach for the synthesis of goniothalesdiol A, leiocarpin A and (+)-goniodiol

A short and efficient syntheses of goniothalesdiol A, leiocarpin A, and (+)-goniodiol are reported by a convergent strategy using tandem aminoxylation-allylation reaction as a key step starting from benzaldehyde.

An efficient total synthesis of (+)-goniodiol

An efficient total synthesis of (+)-goniodiol was illustrated by using Carreira alkynylation and Sharpless asymmetric dihydroxylation as key steps. Georg Thieme Verlag Stuttgart New York.

Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates

The stereoselective synthesis of (+)-goniodiol, a cytotoxic styryllactone, has been accomplished in 10 steps starting from inexpensive and readily available d-manitol and δ-gluconolactone involving the direct and straightforward reaction conditions of Gri

Stereoselective total synthesis of leiocarpin C and (+)-goniodiol

Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-E

The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol

The synthesis of the styryl lactone Leiocarpin C has been achieved in a highly stereoselective manner using Jacobsen's kinetic resolution, Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation as key steps. This is the first total synthesis of Leiocarpin C, and thus establishes for the first time the absolute stereochemistry of this natural product.

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

Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity

All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.

Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis

(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.