2744-05-0

Upstream product

• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 33240-34-5 cyclopentylmagnesium bromide 

Downstream Products

• 88586-06-5 (3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one 
• 788121-64-2 (1S,6R)-6-Hydroxymethyl-cyclohex-3-enecarboxylic acid 
• 56799-24-7 (4R*,5R*)-4-hydroxymethyl-5-vinylcyclohexene 
• 439919-46-7 cis-1,6-dihydroxymethyl-3-cyclohexene 
• 134877-11-5 (+)-(1S,2R)-1-carbomethoxy-2-bromomethyl-4-cyclohexene 
• 134877-10-4 (+/-)-cis-1-carbomethoxy-2-bromomethylcyclohexane 
• 133806-73-2 (+/-)-cis-1-carbomethoxy-2-bromomethylcyclohexane 
• 134877-09-1 (+)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 15111-54-3 (+/-)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 134877-08-0 (-)-cis-1-carbomethoxy-2-methylcyclohexane 
• 7605-54-1 methyl (1S*,2R*)-2-methylcyclohexanecarboxylate 
• 102629-35-6 (1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid 
• 20993-77-5 (+)-(1R,2S)-1-carboxy-2-methylcyclohexane 
• 65376-02-5 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one 

Relevant academic research and scientific papers

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.

Microbial alcohol dehydrogenase screening for enantiopure lactone synthesis: Down-stream process from microtiter plate to bench bioreactor

One-pot conversion with whole cells of bacteria was performed for biooxidation of meso monocyclic (3a-b) and bicyclic diols (3c-e) into corresponding chiral lactones of bicyclo[4.3.0]nonane structure (2a-b) as well as exo- and endo-bridged lactones with the structure of [2.2.1] (3c-d) and [2.2.2] (3e). Micrococcus sp. DSM 30771 was selected as biocatalyst with significant alcohol dehydrogenase activity. Among tested strains, microbial oxidation of meso diols 3a-e catalyzed by Micrococcus sp. afforded enantiomerically pure ((+)-(2S,3R)-2c (ee = 99%), (+)-(2S,3R)-2e (ee = 99%)) or enriched ((+)-(1S,5R)-2a (ee = 90%), (-)-(1S,5R)-2b (ee = 86%), (+)-(2S,3R)-2d (ee = 80%)) lactone moieties. Comparative study with respect to microbial cultivation as well as biooxidation was undertaken to verify agreement of secondary metabolite biosynthesis in different scales: from MTP (4 mL), across shake flask (100 mL) till bioreactor (4 L). The results from biotransformations showed quite similar dependence in oxidation of all substrates 3a-e in MTP and flasks as well, thereby confirmed the validity and reasonable approach of using MTP for preliminary studies.

Syntheses stereoselectives des γ-lactones bicycliques condensees

A highly stereoselective synthesis of trans/trans and cis/trans bicyclic γ-lactones is described using bicyclic dicarboxylic anhydrides.

REDUCTION DES ANHYDRIDES BICYCLIQUES CONDENSES PAR LE BROMURE DE CYCLOPENTYLMAGNESIUM

Greatly different product distributions were observed in the reactions of cyclopentyl- and isopropylmagnesium bromides with cyclohexane-, cyclohex-4-ene- and cyclobutane-1,2 dicarboxylic anhydrides.Cyclopentylmagnesium bromide yielded reduction products with high stereoselectivity whereas the isopropylmagnesium bromide provided the corresponding trans diastereomeric ketoacids via an addition enolization process.