439919-46-7

Upstream product

• 2305-26-2 cis-1,2,3,6-tetrahydrophthalic acid 
• 4841-85-4 cis-4-cyclohexene-1,2-dicarboxylic acid diethyl diester 
• 2744-05-0 8-oxabicyclo[4.3.0]non-3-en-9-one 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 566927-94-4 (4aR,9aS)-7-Benzenesulfonylmethyl-1,4,4a,5,9,9a-hexahydro-6,8-dioxa-benzocycloheptene 
• 85-43-8 1,2,3,6-Tetrahydrophthalic anhydride 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 

Downstream Products

• 3470-42-6 cis-8-oxabicyclo<4.3.0>non-3-ene 
• 954148-36-8 (1R,2S)-[2-[(acetyloxy)methyl]cyclohex-4-en-1-yl]methyl acetate 
• 32970-96-0 cis-(cyclohex-4-ene-1,2-diyl)bis(methylene) bis(4-methylbenzenesulfonate) 
• 93659-64-4 cis-1,2-Bis-carbamoyloxymethyl-cyclohexen-⁽⁴⁾ 
• 15753-50-1 cis-1,2-cyclohexanedimethanol 
• 56799-21-4 cis-6-Hydroxymethyl-3-cyclohexen-1-carbaldehyd 
• 98516-10-0 acetic acid (1R,6S)-6-hydroxymethyl-cyclohex-3-enylmethyl ester 
• 98516-11-1 acetic acid (1S,6R)-6-hydroxymethyl-cyclohex-3-enylmethyl ester 
• 143857-90-3 cis-4,5-bis(pivaloyloxymethyl)cyclohexene 
• 60220-77-1 cis-4,5-bis(benzyloxymethyl)cyclohexene 
• 98516-10-0 Acetic acid (1R,6S)-6-hydroxymethyl-cyclohex-3-enylmethyl ester 
• 15679-28-4 ((1R,6R)-6-(hydroxymethyl)cyclohex-3-enyl)methanol 
• 65376-05-8 (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane 
• 65376-04-7 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid 

Relevant academic research and scientific papers

Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was previously shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofuran units. Herein, we describe the first synthesis of (+)-darwinolide, which features a convergent aldol fragment coupling, an Ireland–Claisen rearrangement, and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.

Thromboxane receptor active analogues based on the 6-oxabicyclo[3.2.1]octane ring system

Prostanoid analogues with a 6-oxabicyclo[3.2.1]octane ring and 3 different types of ω-chain have been synthesized and evaluated for biological activity on thromboxane A2 (TXA2) receptors and prostaglandin I2 (PGI2) receptors. The standard ω-chain analogue 34b is a TXA2 receptor agonist approximately 10-fold less potent than U46619 3, the standard agonist. The O-diphenylmethyloximino-ω'-chain analogue 32 gives a PGI2-like agonist ~5-fold less active than EP 157, the most active molecule in this class. Conversely, 4-arylsemicarbazone ω-chain analogues 35a and 35b show TXA2 antagonism comparable to that obtained with bicyclo[2.2.2]octane and bicyclo[2.2.1]heptane systems containing this type of ω-chain (eg EP 092).

Trisequential photooxygenation reaction: Application to the synthesis of carbasugars

4,5-Dimethylenecyclohex-1-ene was subjected to a photooxygenation reaction to introduce oxygen functionalities. The endoperoxide obtained underwent an ene-reaction to form hydroperoxides with 1,3-diene structures. Further addition of singlet oxygen to the

TRICYCLIC P2-LIGAND CONTAINING POTENT HIV-PROTEASE INHIBITORS

Compounds of formula (I), pharmaceutical compositions comprising compounds of the formula (I), and methods of treating an HIV infection comprising administering an effective amount of one or more compounds of formula (I), or a pharmaceutical composition comprising same.

Structure-Based Design of Highly Potent HIV-1 Protease Inhibitors Containing New Tricyclic Ring P2-Ligands: Design, Synthesis, Biological, and X-ray Structural Studies

We describe here design, synthesis, and biological evaluation of a series of highly potent HIV-1 protease inhibitors containing stereochemically defined and unprecedented tricyclic furanofuran derivatives as P2 ligands in combination with a variety of sulfonamide derivatives as P2′ ligands. These inhibitors were designed to enhance the ligand-backbone binding and van der Waals interactions in the protease active site. A number of inhibitors containing the new P2 ligand, an aminobenzothiazole as the P2′ ligand and a difluorophenylmethyl as the P1 ligand, displayed very potent enzyme inhibitory potency and also showed excellent antiviral activity against a panel of highly multidrug-resistant HIV-1 variants. The tricyclic P2 ligand has been synthesized efficiently in an optically active form using enzymatic desymmetrization of meso-1,2-(dihydroxymethyl)cyclohex-4-ene as the key step. We determined high-resolution X-ray structures of inhibitor-bound HIV-1 protease. These structures revealed extensive interactions with the backbone atoms of HIV-1 protease and provided molecular insights into the binding properties of these new inhibitors.

Stereoselective synthesis of new rac-quercitols containing hydroxymethyl groups as glucosidase inhibitors

Stereoselective and efficient synthesis of hydroxymethyl-substituted rac-quercitols (13–15) was achieved, starting from cis-furan (Kobayashi, 2008) with photooxygenation reaction, which is readily available by the reduction of cis-phtalic anhydride. α- and β-Glucosidase enzyme activity of the target molecules was evaluated and good inhibitor activity was seen. One- and two-dimensional NMR spectroscopy, IR spectroscopy and X-ray crystallography were utilized in the structure characterization of products.

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers

Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.

Truncated borrelidin analogues: Synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation

The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.

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.