The Journal of Organic Chemistry

Synthesis of a model hapten with cyclohexanediol and. alpha.-methylene-. gamma.-butyrolactone groups, a synthetic analog of poison ivy and tulipalin allergens …

H Mattes, C Benezra

文献索引：Mattes, Henri; Benezra, Claude Journal of Organic Chemistry, 1988 , vol. 53, # 12 p. 2732 - 2737

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被引用次数: 28

摘要

Potential skin sensitizers 1 and 1* with two different haptenic ends,(a) a cyclohexanediol group (saturated poison ivy analogue) and (b) an a-methylene-y-butyrolactone moiety (tulipalin A), separated by a nine carbon atoms chain containing a double bond have been prepared. The trans, trans relationship in the substituted cyclohexanediol wa secured by a tandem Michael addition-hydroboration reaction. Contrary to an earlier example of a ...