111136-40-4

Upstream product

• 55848-86-7 Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate 
• 665003-66-7 (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 14371-10-9 (E)-3-phenylpropenal 
• 74590-73-1 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 121712-61-6 methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate 
• 116-11-0 2-Methoxypropene 
• 121786-82-1 (E)-methyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoate 
• 104-55-2 3-phenyl-propenal 
• 105-45-3 acetoacetic acid methyl ester 
• 141928-29-2 Methyl (+/-)-(6E)-5-Hydroxy-3-oxo-7-phenyl-6-heptenoate 

Downstream Products

• 70633-85-1 (4R,6S,1'E)-4-hydroxy-6-(2'-phenylvinyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 70670-14-3 (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one 
• 171598-87-1 (E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate 
• 913255-79-5 methyl 2-((2R,4S,5S,6R)-4,5-dihydroxy-6-phenyltetrahydro-2H-pyran-2-yl)acetate 
• 109519-27-9 methyl (3S^*,5R^*)-3,5-isopropylidenedioxy-7-phenyl-6-heptenoate 

Relevant academic research and scientific papers

Short and efficient chemoenzymatic synthesis of goniothalamin

A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed.

A three-step total synthesis of goniothalesdiol A using a one-pot Sharpless epoxidation/regioselective epoxide ring-opening

Using a one-pot Sharpless asymmetric epoxidation/regioselective epoxide ring-opening as a key step, the protecting-group-free total synthesis of goniothalesdiol A was accomplished in only three steps starting from commercially available trans-cinnamaldehy

Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors

Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

Enzyme-catalyzed Lactonization of Methyl (+/-)-(E)-3,5-Dihydroxy-7-phenyl-6-heptenoates. - A Comparison of the Behaviour of syn- and anti-Compounds

3-Hydroxy lactones with a high enantiomeric excess were obtained by the lipase-catalyzed enantioselective lactonization of racemic syn- and anti-3,5-dihydroxy carboxylic esters.The (5S)-lactones were formed predominantly from both diols with pancreatin as

STUDIES ON THE DIASTEREOSELECTIVE REDUCTION OF β-HYDROXY KETONES TO 1,3-DIOLS WITH COMMON HYDRIDE REAGENTS

Some common reducing agents were employed in the diastereoselective reduction of several β-hydroxy ketones to their corresponding syn-1,3-diols.The use of NaBH4 with a Ti(IV) chelating species produced syn diols with a moderate to good selectivity significantly depending upon the reaction conditions chosen (solvent, temperature, nature of the titanium species).The use of LiAlH4 at low temperature, in the presence of LiI, showed a high selectivity for reduction to syn diols, thus demonstrating a possible chelating role of lithium.Some interesting preliminary results have been also obtained in the diastereoselective reduction of MEM-protected β-alkoxy ketones.

Synthesis, biological profile, and quantitative structure - Activity relationship of a series of novel 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors

A series of 9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(alkyltetrazol-5-yl)-6,8-nonad ienoic acid derivatives 1 were synthesized and found to inhibit competitively the enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase. The analogues having 1N-methyltetrazol-5-yl attached to the C8-position (3a, 4a, R1 = R2 = F) are the most active in suppressing cholesterol biosynthesis in both in vitro and in vivo models: the IC50 for the chiral form of 3a is 19 nM, K(i) = 4.3 x 10-9 M when K(m) for HMG-CoA is 28 x 10-6 M; the ED50 (oral) value corresponding to the lactone derivative (4a, BMY 22089) is approximately 0.1 mg/kg. Further, BMY 21950 is nearly 2 orders of magnitude more active in parenchymal hepatocytes, from which most of the serum cholesterol originates, than in other cell preparations (such as spleen, testes, ileum, adrenal, and ocular lens epithelial cells; Table III). This apparent tissue specificity may be highly beneficial since the blocking of cholesterol biosynthesis in other vital organs could eventually lead to undesirable side effects. In addition to the chemical synthesis and biological evaluation, a theoretical study aimed at relating the HMG-CoA reductase inhibitory potency to the three-dimensional structure of the inhibitors was undertaken. With a combination of molecular mapping and 3D-QSAR techniques, it was possible to determine a logical candidate for the conformation of the bound inhibitor and to quantitatively relate inhibitory potency to the shape and size of both the binding site and the C8-substituent.

A FACILE ENTRY TO β,δ-DIKETO AND syn-β,δ-DIHYDROXY ESTERS

Reaction of N-metoxy-N-methyl amides with the dianions of acetoacetates gives β,δ-diketo esters in yield of synthetic use, and the diketo esters were selectively reduced to syn-β,δ-dihydroxy esters, key intermediates of synthetic HMG-CoA reductase inhibit

A Novel Method for the In Situ Generation of Alkoxydialkylboranes and Their Use in the Selective Preparation of 1,3-Syn Diols

An in situ method for generating Et2BOCH3 from triethylborane and methanol without using any other catalysts is described.Using the Et2BOCH3 thus generated as a chelating agent, syn 1,3-diols are prepared in > 98 percent stereochemical purity by reducing β-hydroxy-ketones with sodium borohydride

1,3-SYN DIASTEREOSELECTIVE REDUCTION OF β-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES

Sodium borohydride reduction of β-hydroxyketones in presence of alkoxydialkylboranes 1-7 as complexing agents, produced 1,3-syn diols in at least 98:2 ratio.As illustrated with examples 8-17 this method is quite general and superior to those described in

Stereoselective Reduction of δ-Hydroxy-β-ketoesters

The reduction of δ-hydroxy-β-ketoesters 1 was investigated with three different reducing agents.In several instances, high selectivity in favor of syn-1,3-diols was observed.