124649-26-9

Usage

Uses

Used in Agriculture:
(+)-Tuberonic acid is used as a plant growth regulator for promoting tuber formation in crops such as potatoes. Its tuber-inducing properties make it a valuable tool for enhancing crop yield and quality.
Used in Fragrance Industry:
(+)-Tuberonic acid is used as a key ingredient in the synthesis of Jasmonic Acid, which is a major constituent of the essential oil of Jasmine. It plays a crucial role in the fragrance industry, contributing to the production of various perfumes, scented products, and aromatherapy oils.

InChI:InChI=1/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1

Upstream product

• 68931-53-3 5'-Hydroxythiojasmonsaeure-S-t-butylester 
• 81761-06-0 methyl (1S*,2S*)-2-[(2Z)-5-hydroxy-2-pentenyl]-3-oxocyclopentaneacetate 
• 51442-80-9 5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol 
• 92775-68-3 1-methanesulfonyloxy-5-(tetrahydro-2-pyranyloxy)pent-2-yne 
• 932391-42-9 2-((1R,2S)-3-oxo-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)-pent-2-enyl)cyclopentyl)ethanoic acid 
• 68931-47-5 [(1S,2S)-2-(5-Hydroxy-pent-2-ynyl)-3-oxo-cyclopentyl]-thioacetic acid S-tert-butyl ester 
• 81760-96-5 2,5-diethoxycarbonyl-3-methoxycarbonylmethyl-2-(5-tetrahydropyranyloxy-2-pentynyl)cyclopentanone 
• 51557-87-0 trans-2-allyl-1-cyclopentanone-3-acetic acid methyl ester 
• 81760-94-3 diethyl 2-(tetrahydropyranyloxy-2-pentynyl)-3-oxopentanedioate 
• 85604-61-1 2-allyl-2,5-diethoxycarbonyl-4-methoxycarbonylmethylcyclopentanone 

Downstream Products

• 140631-27-2 [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid 
• 68931-43-1 (Z)-1,2-trans-8,13-dioxo-7-oxabicyclo<8.3.0>tridec-3-ene 

Relevant academic research and scientific papers

First total synthesis of tuberonic acid

A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2{double bond, long}CHMgBr, LiCl, and a CuCN catalyst to produce the SN2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by 1H NMR spectroscopy.

Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser-Claisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH 2)Me]+Br- followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1).

Synthesis of Jasmine Ketolactone

The synthesis of jasmine ketolactone 3, a minor component of Italian jasmine oil, via the intramolecular Michael reaction is described.