54595-10-7

Upstream product

• 126783-82-2 (1R,2S,3R,2''Z)-3-Hydroxy-1-(2-hydroxyethyl)-2-(2-pentenyl)cyclopentan 
• 807355-32-4 (1R,5S,6R)-6-methoxycarbonylmethyl-3-methoxy-2-oxabicyclo<3.3.0>octane 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 53921-55-4 ((3aS,6aR)-2-Hydroxy-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid 
• 807355-33-5 (1R,5S,6R)-6-methoxycarbonylmethyl-3-hydroxy-2-oxabicyclo<3.3.0>octane 
• 139448-28-5 (+)-(1R,2S,3R)-methyl 3-hydroxy-2-(2-triphenylmethoxyethyl)-1-cyclopentaneacetate 
• 110-71-4 1,2-dimethoxyethane 
• 95722-42-2 (+)-7-iso-jasmonic acid methyl ester 
• 118285-12-4 dimethyl 2-(2,2-dimethoxyethyl)-2-cyclopentenylmalonate 
• 118285-13-5 methyl 2-(2,2-dimethoxyethyl)-2-cyclopentenylacetate 
• 118285-11-3 2-(2,2-dimethoxyethyl)-2-cyclopentenylacetate 
• 118285-10-2 2-(2,2-Dimethoxy-ethyl)-cyclopent-2-enol 
• 112532-64-6 2-(2,2-dimethoxyethyl)-2-cyclopenten-1-one 
• 51557-84-7 2-chloro-2-allyl-1,3-cyclohexanedione 

Downstream Products

• 1211-29-6 methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate 
• 34027-33-3 (+/-)-Cucurbic acid 
• 34027-33-3 [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid 
• 1211-29-6 Methyl jasmonate 

Relevant academic research and scientific papers

A general enantioselective approach to jasmonoid fragrances: Synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione

Methyl dihydrojasmonate 1 and magnolione 3 are of both academic and industrial interest. In this paper, we describe a flexible, high-yielding route to diastereomerically pure (+)-cis-(1R,2S)-methyl dihydrojasmonate 1 and the first synthesis of (+)-cis-(1R

Easy preparation of methyl 7-epi-jasmonate and four stereoisomers of methyl cucurbate, and assessment of the stereogenic effect of jasmonate on phytohormonal activities

To test the stereogenic effect of jasmonate on phytohormonal activities, methyl 7-epi-jasmonate (1b) and four stereoisomers of methyl cucurbate were easily prepared in racemic form: epimerization at the C-7 position of a commercially available methyl jasmonate (2b) with a base and subsequent fractional distillation gave a 46:54 mixture of 1b and 2b, whose reduction gave a mixture of methyl cucurbates (3-6). This synthetic chemistry was supplemented by molecular modeling and an NMR study on 1b and 2b. An assessment of the inhibitory activities of the prepared jasmonates on growth of the second leaf sheath of rice and on seed germination of cress clarified that the cis-configuration of the C-3 and C-7 side chains of jasmonate was an important factor for the high activities. In inhibiting the seed germination of cress, methyl 6-epi-cucurbate (4) exhibited activity that was markedly higher than the other compounds tested, showing that the stereochemistry at C-6 as well as at C-3 and C-7 was strictly recognized by this bioassay.

Synthesis of both the enantiomers of methyl epijasmonate

Both the pure enantiomers of methyl epijasmonate 1 with potato-tuber inducing activity were synthesized stereoselectively starting from 2-oxabicyclo[3.3.0]-oct-6-en-3-one 6 in 20% yield through 11 steps.

Synthesis of Chiral Methyl Cucurbate and Its Analogs

Natural (+)-(1R,2S,3S)-methyl cucurbate (1b) and the (-)-δ-lactone of 3-epi-cucurbic acid (16) were synthesized from (+)-(1R,6S,7R)-bicyclonon-3-en-7-ol (5).Asymmetric hydrolysis of the acetate (8) of (+/-)-5 with pancreatin gave optically pure the

Chemistry and Stereochemistry of Iridoids, XIII. - Synthesis of Enantiomerically Pure Methyl (1R,2S,2''Z)-(+)-Jasmonate Starting from Catalpol

Enantiomerically pure methyl (1R,2S,2''Z)(+)-jasmonate (2), which was recognized as a component of the fragrance of the jasmine flower oil, was synthesized starting from catalpol (3). 2 is easily epimerized to 1.Thus, it is necessary to use very mild conditions in the course of the synthesis and purification.These results raise the question whether 2 exists as a natural product in the flower of jasmine and 1 arises during the isolation.

An Efficient and Stereocontrolled Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Cucurbic Acid

The total synthesis of epijasmonoids, (+/-)-methyl epijasmonate and (+/-)-cucurbic acid, starting from norbornene was described, where a key intermediate, 5β-hydroxy-2β-methoxycarbonylmethylcyclopentane 1β-acetic acid γ-lactone was efficiently prepared via a highly regioselective Baeyer-Villiger oxidation of 7-syn-substituted norbornanone based on remote substituent control.

Synthesis of (+/-)-Methyl Epijasmonate and (+/-)-Methyl Cucurbate

A novel synthesis of (+/-)-methyl epijasomonate (2) and the first synthesis of (+/-)-methyl cucurbate (4) were achieved startig from 2-allocyclohexane-1,3-dione (8).The synthetic epimer 2 had a stronger jasmin flavor than the trans-isomer 1 with 95percent purity.

An Efficient Total Synthesis of (+/-)-Methyl Jasmonate

A short synthesis of Methyl dl-Jasmonate from bicyclo nona-3,8-diene is described.