Methyl -famesoate

Natural products containing the isoprene unit can be prepared in this way. Methyl famesoates have been synthesized from geranyl halides and 1-carbomethoxyallylnickel halides (example 4, Table III). 

The mandibular organ-inhibiting hormone of the crab Cancer pagurus produces two neurohormones that inhibit the secretion of methyl famesoate, which is thought to function as the juvenile hormone in crustaceans 357... 

Homola E, Chang ES (1997) Methyl famesoate crustacean juvenile hormone in search of functions. Comp Biochem Physiol B 117 347-356... 

Laufer H, Biggers WJ (2001) Unifying concepts learned from methyl famesoate for invertebrate reproduction and post-embryonic development. Am Zool 41 442 -57... 

Chemical syntheses of brominated polycyclic compounds have been developed over the past 50 years [42], In 1966, the first bromonium ion-induced polyene cyclization was demonstrated by van Tamelen s group [43]. The reaction of methyl famesoate with A-bromosuccinimide (NBS) in a mixture of THE and H O at 0°C gave an isomeric mixture of brominated bicyclic esters, although the yield was very low. This may has been due to the low site selectivity of the reaction of the brominating reagent with terminal or internal olefins (Scheme 9.26). 

It is interesting that methyl famesoate is present in some Crustacea, and a mixture of methyl famesoate and JH III in the embryos of primitive insects such as cockroaches. There appears to be a kind of evolution through appearance of successive epoxidases of the cytochrome P450 family. Some form of juvenile hormone is present in ticks and other arthropods. 

The hormone that inhibits molting is methyl famesoate, which is very similar to the juvenile hormone of insects it inhibits the functioning of the Y organ between two successive molts. In insects this second hormone is... 

Other biological properties have been identified for methyl famesoate and cmstecdysone, in particular the control of ovarian maturation in the shrimp Penaeus vannamei (Chan, 1995), osmoregulation in the crab Carcinus mamas (Lovett et al., 2001), and growth and differentiation in the spider crab Libinia emarginata (Laufer et al., 2002). 

Lovett, D.L., Verzi, M.P., Clifford, P.D., and Borst, D.W. (2001) Hemolymph levels of methyl-famesoate increase in response to osmotic stress in the green crab, Carcinus maenas. Comp. Biochem. Physiol, 128A, 299-306. 

Tobe, S.S., Young, D.A, and Khoo, H.W. (1989a) Production of methyl famesoate by the mandibular organs of the mud crab, Scylla serrata validation of a radiochemical assay. Gen. Comp. Endocrinol., 73,342-353. 

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