Methyl farnesate

Komal et (Ref. 53) found gc-ms evidence of the sesquiterpenes 6 sellnene (54), methyl farnesate, farnesyl acetate (55), and farnesol (56) present In an Inhibitory fraction Isolated from water nutgrass (Cyperus serotinus ). This fraction at 300 ppm Inhibited lettuce germination and also Inhibited growth of lettuce and rice seedlings as well as nutgrass Itself. The authors conclude that the sesquiterpenes are responsible for the observed allelopathlc effects. 

CycHzation of methyl farnesate. Reaction of methyl irons,trans-fasiKsa.Vo (1) with NBS and cupric acetate in r-butyl alcohol-HOAc yields the cyclic product (2) in 12% yield. The product was transformed into snyderol (3), a sesquiterpene in Laurencia snyderae. ... 

Preferential addition. A soln. of mercuric acetate in methanol added during 15 min. to a stirred ice-cold soln. of methyl farnesate in the same solvent, allowed to stand 0.5 hr., methanolic KOH added followed by NaBH4 in small portions, and stirring continued 0.5 hr. methyl ll-methoxy-3,7,ll-trimethyl-2,6-dodecadie-noate. Y 74%. Also ethoxy analog s. N. Wakabayashi, J. Med. Chem. 12, 191 (1969). 

Gonzalez, A.G., Martin, J.D., Perez, C., and Ramirez, MA. (1976) Bromonium ion-induced cyclization of methyl farnesate appUcation to the synthesis of snyderol. Tetrahedron Lett., 2,137-138. 

Methyl 4 6-0-ethylidene-2 3-0-oxido-diethylidene- 8-D-glucopyranoside, 4 Methyl ethyl ketone, 450 Methyl irons,irons-farnesate, 227... 

It should be pointed out that manganese dioxide is a mild oxidant that usually converts primary allylic alcohols into conjugated aldehydes without significant further oxidation to carboxylic acids." However, in the presence of HCN and cyanide, the a, -unsaturated aldehydes could be converted into cyanohydrins, which are susceptible to the oxidation of Mn02 to acyl cyanides. In the presence of an alcohol, the a,j8-unsaturated esters are obtained. It should be emphasized that this reaction works only for a,j8-unsaturated aldehydes and will not cause any cis-trans isomerization for the a,/3-unsaturated double bond. For example, benzaldehyde (> 95%), cinnamaldehyde (> 95%), furfural (> 95%), geranial (85-95%), and farnesal (> 95%) have all been transformed into the corresponding methyl esters. ... 

C7 Diploptera punctata Farnesol, farnesal, famesoic acid, methyl farneso- [251] ... 

A1 Musca domestica Farnesal, methyl farnesoate, JHI, JHIII, steroid [272] ... 

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