Famesene

Alkenes are hydrocarbons that contain a carbon-carbon double bond. A carbon-carbon double bond is both an important structural unit and an important functional group in organic chemistry. The shape of an organic molecule is influenced by the presence of this bond, and the double bond is the site of most of the chemical reactions that alkenes undergo. Some representative alkenes include isobutylene (an industrial chemical), a-pinene (a fragrant liquid obtained from pine trees), and famesene (a naturally occuning alkene with three double bonds). 

Since these make up 80% of the urinary volatiles and elicit several specific behavioural and endocrine responses, they are clearly a major signal source. The range of effects induced by these compounds suggests that famesenes are likely to act via both the MOS and the AOS. 

The sesquiterpene w-famesene, 51, a primary aroma component which occurs in the skin of apples39 and other fruits40, attractant and oviposition stimulant to Laspeyresia pomonella41 42, has been deuteriated at Cq) and at C(4) (equations 19 and 20), for study of the induction of superficial scald of apples43. 

Zea mays Leaves, Spodoptera littoralis [31] Leaves, Spodoptera littoralis [31] (35)-( )-nerolidol synthase (3/ )-(it)-nerolidol/(ii)-f - famesene/( , )-famesol synthase tpsl [62] [64]... 

Myrcene, ocimene, and famesene, are present in many fruits and essential oils, but find only limited use in perfumery. 

Artimisia lactiflora Wallich Flavonoid glycoside, coumarin, lactiflorenol, spathulenol, s-guaiazulene, beta-guaienen, trans- 3-famesene, iram-caryophyllene, limonene, elemene, copaene, myrcene.57 Diuretic, regulate menstruation, treat headache, high blood pressure. 

Several natural products (Scheme 60) have been synthesized in vitro via singlet oxygen ene reactions. For example, clavukerin C was prepared202 in racemic form, in a biomimetic synthesis by Kim and Pak, whereas a-famesene hydroperoxide was obtained203 starting from geraniol. 

The Rh/tppts catalysed C-C coupling reaction (Figure 17) has a broad scope and numerous conjugated dienes e.g. isoprene and P-famesene can be used as starting materials with other active methylene compounds e.g. acetylacetone and barbituric acid.506 Figure 18 depicts the Rh/tppts/Na2C03-catalysed isopreny-lation of barbituric acid which proceeds at room temperature in an H20/MeOH (75/25) solvent mixture.506... 

Numerous dienes can be used as reactants, e.g., isoprene, myrcene, and famesene, and several compounds can be used as active methylene compounds. The reaction proceeds in an aqueous liquid-liquid system, with the conversion regulated by the time of contact between the phases, which is controlled by the stirring. The organic products are easily separated by simple decantation, and the aqueous phase containing the catalyst can be recycled. This reaction was industrialized to produce intermediates for vitamin E such as geranylacetone. The capadty is about 1000 tons/year. 

Rostelien T., Borg-Karlson A. K. and Mustaparta H. (2000b) Selective receptor neurone responses to E-beta-ocimene, beta-myrcene, E,E-alpha-famesene and homo-famesene in the moth Heliothis virescens, identified by gas chromatography linked to electrophysiology. J. Comp Physiol. A 186(9), 833-847. 

Trans P-sinensal 441 is obtained from the aldehyde 438 prepared by selective ozonolysis of trans-famesene 437. Wittig olefmation of 438 with 1-formylethylidene-phosphorane 440 gives trans P-sinensal 441. Reaction of 438 with 1-ethoxycarbonyl-ethylidene-triphenylphosphorane 439 yields the ethyl ester 442, from which 441 can also be obtained 237 (Scheme 77). Furthermore, a working group of the BASF synthesized a-sinensal 443 and p-sinensal 441 using Wittig reactions 238). 

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