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    • 91. 发明专利
    • PRODUCTION OF 8ALPHA,12-EPOXY-13,14,15,16-TETRANORLABDANE
    • JPS63162683A
    • 1988-07-06
    • JP31451586
    • 1986-12-24
    • HARIMA CHEMICALS INC
    • ONO MASAJIKINE MASATO
    • C07D307/92
    • PURPOSE:To obtain the titled compound having amber smell and useful for perfumery, etc., at a low cost, by subjecting abietic acid successively to oxidation, esterification, decomposition of aldehyde group, reduction of ketone group and ester group, vinylation by ultraviolet irradiation, oxidative decomposition and cyclization. CONSTITUTION:The objective compound can be produced by (1) oxidizing abietic acid to effect the ring-opening at the double bond adjacent to propyl group and the esterification of the carboxylic acid group to form a compound of formula I (R is alkyl), (2) decomposing the 2-aldehyde group of the compound to obtain a mixture of the compounds of formula II and formula III, (3) decomposing and reducing the 1-side chain to hydroxyethylene group, (4) reducing the 5-ester group to hydroxymethylene group to obtain a mixture of the compounds of formula IV and formula V, (5) masking the 1- and 5-OH groups and irradiating the compounds with ultraviolet radiation to convert the 2-position to vinyl group, (6) carrying out the oxidative decomposition of the 2-position, (7) forming an oxide ring between the OH group of the 1-side chain and the 2-OH group of the resultant compound of formula VI and finally (8) reducing the 6-hydroxymethylene group to methyl group.