70633-85-1

Upstream product

• 103338-09-6 methyl (E,3S^*,5R^*)-3,5-dihydroxy-7-phenyl-6-heptenoate 
• 121786-82-1 (E)-methyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoate 
• 143900-72-5 (E)-(3R,5S)-3,5-Dihydroxy-7-phenyl-hept-6-enoic acid tert-butyl ester 
• 135942-67-5 (4S)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3R,5S)-3,5-dihydroxy-7-phenyl-6-heptenoate 
• 141928-29-2 Methyl (+/-)-(6E)-5-Hydroxy-3-oxo-7-phenyl-6-heptenoate 
• 143840-67-9 (S)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester 
• 143800-10-6 [(4R,6S)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 121980-44-7 methyl (3R)-3-<(t-butyl)dimethylsilyloxy>hex-5-enoate 
• 121980-45-8 (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate 
• 121980-46-9 methyl (3R)-3-<(t-butyl)dimethylsilyloxy>-7-phenylhept-5-enoate 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 
• 121980-48-1 (Z)-(R)-3-Hydroxy-7-phenyl-hept-5-enoic acid 
• 92081-23-7 methyl erythro-3,5-bis<(diphenyl-tert-butylsilyl)oxy>-6-oxohexanoate 

Downstream Products

• 22639-28-7 (R)-goniothalamin 
• 118204-01-6 (6R)-6-<(Z)-styryl>-5,6-dihydro-2H-pyran-2-one 
• 118117-14-9 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-styryl)-tetrahydro-pyran-2-one 
• 118117-14-9 (4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-styryl)-tetrahydro-pyran-2-one 
• 118117-14-9 (4S,6R)-3,4,5,6-tetrahydro-6-(2-phenylethenyl)-4-dimethyl-t-butylsilyloxy-2H-pyran-2-one 

Relevant academic research and scientific papers

Asymmetric synthesis of (-)-leiocarpin A via (-)-(S)-goniothalamin employing Julia-Kocienski olefination

A concise and enantioselective syntheses of antileukemic natural products such as (-)-(S)-goniothalamin and (-)-leiocarpin A has been accomplished in excellent yields. By employing reported conditions on suitable substrates via Julia-Kocienski olefination

Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs

Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the correspondi

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

New chiral blocks for introducing the side chain of HMG-CoA reductase inhibitors

A couple of versatile building blocks (8 and 9) of the side chain portion found in many HMG-CoA reductase inhibitors have been prepared. The successful introduction of the side chain to an aromatic ring by 8 or 9 has been demonstrated.

Enzymes in Organic Synthesis, 11.- Enantioselective Lactonization of Methyl 3,5-Dihydroxyalkanoates. - An Access to (3R,5S,6E)-3-Hydroxy-7-phenyl-6-hepten-5-olide by Enzyme-Catalyzed Kinetic Resolution in Organic Solvents

By enzyme-catalyzed intramolecular transesterfication methyl (+/-)-(3R*,5S*,6E)-3,5-dihydroxy-7-phenyl-6-heptenoate (rac-4) can be enantioselectively converted into the δ-lactone 5.An enantiomeric excess of 80percent was obtained by

Stereocontrolled Route to the δ-Benzylidenemethyl-β-hydroxy-δ-lactone System Utilizing a New Chiral Epoxyacetylene Building Block

Stereocontrolled route to the δ-benzylidenemethyl-β-hydroxy-δ-lactone system has been developed utilizing a new epoxyacetylene building block prepared from optically active epichlorohydrin.The present synthesis allowed efficient construction of goniothalamin in natural and unnatural forms and its 3-hydroxy derivative having the essential anti-β/δ-stereochemistry for HMG Co-A reductase inhibition.

An Alternative Approach to Mevinic Acid Analogues from Methyl (3R)-(-)-3-Hydroxyhex-5-enoate and an Extension to Unambiguous Syntheses of (6R)-(+)- and (6S)-(-)-Goniothalamin

Ozonolysis of the 3-silyloxyhexenoate 12, derived from the yeast reduction product methyl (3R)-(-)-3-hydroxyhex-5-enoate 6 and having an enantiomeric enrichment of 78percent, followed by Wittig homologation and selenolactonization leads to the unsaturated mevinic acid analogues 17 and 18.Subsequent dehydration gives both enantiomers of the natural product goniothalamin 20 and 21.

SYNTHESIS OF THE 5,6-DIHYDRO-2-PYRONE MOIETY OF (+)-ANAMARIN

The α,β-unsaturated δ-lactone (+)-goniothalamin (18E) and its Z-isomer (18Z), which contain the lactonic moiety of (+)-anamarin (1), have been synthesized from the known 1,2-O-isopropylidene 3-deoxy-α-D-glucofuranose (7).In the key step, methyl 3,5-dideoxy-β-D-glucofuranuronate (15) was treated with benzylidenetriphenylphosphorane in dimethyl sulphoxide to give the E- and Z-β-hydroxy δ-lactones (17).These were then transformed into the 5,6-dihydro-2-pyrones (18), and also into the aldehyde (20), intended for use in a total synthesis of (+)-anamarin (1).