19683-98-8

Usage

InChI:InChI=1/C16H24O5/c1-10(2)5-6-12-14(3,21-12)16(18)13(19-4)11(17)7-8-15(16)9-20-15/h5,12-13,18H,6-9H2,1-4H3/t12-,13-,14-,15+,16+/m1/s1

Upstream product

• 214688-36-5 FOS-34 
• 870862-62-7 (3S,4R,5S)-4-((E)-1',5'-dimethylhexa-1',4'-dienyl)-4-hydroxy-5-methoxy-1-oxaspiro[2,5]octan-6-one 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 157727-76-9 C₈H₁₃Li 
• 215370-56-2 (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol 
• 166374-52-3 (3S,4S,5S,6R)-5-Methoxy-6-triethylsilanyloxy-1-oxa-spiro[2.5]octan-4-ol 
• 166184-48-1 (3R,4R,5R,6R)-4-(1',5'-dimethylhexa-1',4'-dienyl)-5-methoxy-6-triethylsiloxy-1-oxaspiro<2.5>octan-4-ol 
• 166184-47-0 (3R,5R,6R)-5-methoxy-6-triethylsiloxy-1-oxaspiro<2.5>octan-4-one 
• 91738-34-0 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 870862-60-5 (1S,2S,3R,4R)-1-(triethylsilyloxymethyl)-2,4-di(triethylsilyloxy)-3-methoxy-1-cyclohexanol 
• 870862-57-0 (1R,2R,3S,4S)-1-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexane 
• 870862-47-8 (2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose 
• 870862-49-0 (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-3-methoxy-6-heptene 
• 870862-48-9 (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol 

Related news

Research PaperSelective inhibition of amino-terminal methionine processing by TNP-470 and ovalicin (cas 19683-98-8) in endothelial cells09/09/2019

Background: The angiogenesis inhibitors TNP-470 and ovalicin potently suppress endothelial cell growth. Both drugs also specifically inhibit methionine aminopeptidase 2 (MetAP2) in vitro. Inhibition of MetAP2 and changes in initiator methionine removal in drug-treated endothelial cells have not ...detailed

The biosynthesis of ovalicin (cas 19683-98-8) from β-trans-bergamotene09/07/2019

Feeding of [12, 13-13C]-β-trans-bergamotene to cultures of Pseudeurotium ovalis resulted in labeling of C-12 and C-13 of the antibiotic ovalicin, as established by 13C NMR.detailed

QSAR of the inhibition of angiogenesis by TNP-470 and ovalicin (cas 19683-98-8) analogues: another example of an allosteric interaction09/06/2019

QSAR have been formulated for variations of TNP-470 and Ovalicin on various cell lines. In the examples of mouse lymphocyte cells and bovine endothelial cells the results suggest an allosteric interaction. These results are compared with the binding of nitrobenzene to hemoglobin in rats in vivo....detailed

Synthetic analogues of TNP-470 and ovalicin (cas 19683-98-8) reveal a common molecular basis for inhibition of angiogenesis and immunosuppression109/05/2019

TNP-470 (1), a synthetic derivative of the natural product fumagillin (2), potently inhibits angiogenesis in vivo and the growth of endothelial cell cultures in vitro. The structurally related natural product ovalicin (3) also inhibits angiogenesis but possesses potent immunosuppressive activity...detailed

Simple and efficient synthesis of highly functionalized cyclohexanes; formal total synthesis of ovalicin (cas 19683-98-8) and fumagillin09/04/2019

Two chiral cyclohexanes 4 and 6, which are key intermediates for the total synthesis of ovalicin 1 and fumagillin 2, respectively, were synthesized from (2R,3S) 1,2-epoxy-4-penten-3-ol. The key steps involve an efficient construction of divinylalcohol 7 using methallyl Grignard reagent 9c, and a...detailed

A novel stereoselective route to a fumagillin and ovalicin (cas 19683-98-8) synthetic intermediate09/03/2019

A strategy using a highly stereoselective Claisen-Ireland rearrangement followed by a Grubbs metathesis afforded in a good overall yield after further functionalisation a potentially synthetic precursor of fumagillin and ovalicin.detailed

Relevant academic research and scientific papers

Stereoselective total synthesis of (-)-Ovalicin

A new synthetic route for epoxyketone 3 is described, which is a key intermediate in Bartons synthesis of ovalicin (1), a powerful anti-angiogenetic inhibitor, from commercially available d-ribose. The key reactions involved in this synthesis are ring-closing metathesis, Rubottom oxidation and Corey-Chaykovsky epoxidation. The subsequent transformations are carried out according to Bartons strategy to complete the total synthesis of (-)-ovalicin. Georg Thieme Verlag Stuttgart New York.

A diels-alder approach to (-)-ovalicin

A round at the Oval: The antiangiogenic activity of the natural product ovalicin has sparked significant interest. A highly efficient enantio- and diastereoselective total synthesis of ovalicin proved successful in which the key step involved an endo sele

Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin

(Chemical Equation Presented) L-Proline-mediated α-aminoxylation is a key step in the enantio- and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, an

Synthesis of ovalicin starting from D-mannose

A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained f

Total synthesis of (-)-ovalicin and analogues from L-quebrachitol

We describe here the first chiral total synthesis of (-)-ovalicin and the synthesis of several related analogues, from the naturally occuring cyclitol L-quebrachitol.

Total synthesis of (-)-Ovalicine from L-Quebrachitol

The first chiral synthesis of (-)-Ovalicine from commercially available L-Quebrachitol in 16 steps and an overall yield of 3.5% is reported.