459-67-6

Usage

Uses

Used in Pharmaceutical Industry:
Hydnocarpic acid is used as a therapeutic agent for the treatment of leprosy, a chronic infectious disease caused by Mycobacterium leprae. Its bioactive properties contribute to the management and alleviation of symptoms associated with leprosy.

InChI:InChI=1/C16H28O2/c17-16(18)14-8-6-4-2-1-3-5-7-11-15-12-9-10-13-15/h9,12,15H,1-8,10-11,13-14H2,(H,17,18)/t15-/m0/s1

Upstream product

• 96-40-2 2-cyclopenten-1-yl chloride 
• 7766-50-9 1-undecen-11-ylbromide 
• 5587-77-9 11-((R)-cyclopent-2-enyl)undecan-1-ol 

Downstream Products

• 3552-12-3 1-((R)-cyclopenten-2-yl)-undecanoic acid-⁽¹¹⁾-ethyl ester 

Relevant academic research and scientific papers

ASYMMETRIC SYNTHESIS OF CHIRAL COMPOUNDS

The present invention provides processes for the production of chiral compounds in a stereoisomeric excess, the processes comprising: (i) contacting a first compound comprising an alkene or alkyne bond with a hydrometallating agent, wherein the first compound and the hydrometallating agent are contacted under conditions such that the first compound is hydrometallated by said hydrometallating agent; and (ii) contacting the hydrometallated first compound with a second compound comprising an allylic group, wherein the hydrometallated first compound and the second compound are contacted under conditions such that they undergo an asymmetric allylic alkylation reaction in which a carbon atom of the hydrometallated first compound binds to a carbon atom of said allylic group, forming a stereoisomeric excess of a compound having a chiral centre in an allylic position, said chiral centre being located at the carbon atom bound by said first compound, wherein said asymmetric allylic alkylation reaction is performed in the presence of a metal catalyst comprising a chiral ligand. In particular, the present invention provides processes for the production of a stereoisomeric excess of a compound of the formula (IA), (IB), (IA') or (IB') as defined herein.

Non-stabilized nucleophiles in Cu-catalysed dynamic kinetic asymmetric allylic alkylation

The development of new reactions forming asymmetric carbon-carbon bonds has enabled chemists to synthesize a broad range of important carbon-containing molecules, including pharmaceutical agents, fragrances and polymers1. Most strategies to obtain enantiomerically enriched molecules rely on either generating new stereogenic centres fromprochiral substratesor resolving racemicmixtures of enantiomers.Analternative strategy-dynamic kinetic asymmetric transformation-involves the transformation of a racemic starting material into a single enantiomer product, with greater than 50 per centmaximumyield2,3. The use of stabilized nucleophiles (pKaa is the acid dissociation constant) in palladium-catalysed asymmetric allylic alkylation reactions has proved to be extremely versatile in these processes4,5. Conversely, the use of non-stabilized nucleophiles insuch reactions is difficultand remains a key challenge6-9. Herewe report a copper-catalyseddynamic kinetic asymmetric transformation using racemic substrates and alkyl nucleophiles. These nucleophiles have a pKa of ≥ 50, more than 25 orders of magnitude more basic than the nucleophiles that are typically used in such transformations. Organometallic reagents are generatedin situ fromalkenes byhydrometallation and givehighly enantioenriched productsunder mild reaction conditions. The method is used to synthesize natural products that possess activity against tuberculosis and leprosy, and an inhibitor ofpara-aminobenzoate biosynthesis. Mechanistic studies indicate that the reaction proceeds through a rapidly isomerizing intermediate.We anticipate that this approach will be a valuable complement to existing asymmetric catalytic methods.