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The total synthesis of different isomers and analogues of poison ivy urushiol is described. These include the positional isomers 1-5 and the nitrogen-containing analogues 6 and 8 and their mesylamino derivatives 7 and 9. 3,4-Dimethoxybenzaldehyde, m-dimethoxybenzene, resorcinol, and p-dimethoxybenzene were used as starting materials for compounds 1, 2, 3, and 4, respectively. Compound 5 is prepared by catalytic hydrogenation of bilobol isolated from Ginkgo biloba. Compounds 6 and 7 were prepared from anacardic acid as the starting material while compounds 8 and 9 were prepared from phenol as the starting material. Compounds 1-9 were tested for their ability to cross-react with poison ivy urushiol in sensitized guinea pigs. Compounds 6 and 8 were reactive at the 10-microgram dose level when applied topically, while compound 1 was a skin irritant at that dose. On the other hand, compounds 2-5, 7, and 9 showed no cross-reactivity up to the 30-micrograms dose level. Structural requirements for cross allergenicity are discussed.

Ausgehend von Phenol (I), m‐ (XV) und p‐Dimethoxybenzol (XX), Veratrumaldehyd (X) und Resorcin (XVIII) werden nach dem im Schema angegebenen Reaktionsfolgen einige Isomere wie (XIV), (XIX) und (XXII) und einige Analoge wie (VII), (IX) und (XVII) des 3‐Pentadecylcatechols (XXIII) (PDC) hergestellt.

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