Synthesis of isoprenoid 1,5-dienes

Details Synthesis of isoprenoid 1,5-dienes Synthesis of isoprenoid 1,5-dienes

1976-05-26

1977-12-20

Douglas, Winston A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260526N, 260514L, 252522, C11C 100, C07C 5300

Patent

active

040641503

ABSTRACT:
Aliphatic acids containing an isoprenoid 1,5-diene moiety are prepared in high yields by the selective gamma alkylation of .alpha.,.beta.-unsaturated acids with allylic electrophiles. The gamma-regioselectivity of the alkylation is controlled by the use of the dicopper(I) dienolates prepared from the .alpha.,.beta.-unsaturated acids. The method offers a particularly facile means for synthesizing isoprenoid 1,5-diene natural products such as farnesoic acid by alkylation of senecioic acid with geranyl bromide; geranoic acid by alkylation of senecioic acid with 3,3-dimethallyl bromide; and dl-lanceol by alkylation of tiglic acid with an allylic bromide derived from dl-limonene. Such products find use in the synthesis of insect pheremones, insect juvenile hormones, and components of perfumes.

REFERENCES:
patent: 3971827 (1976-07-01), Baran et al.
Katzenellenbogen, J., Journal of the American Chemical Society, vol. 96, pp. 5662-5663, (1974).

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