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ECB-ART-30636
Acta Chem Scand B 1977 Jan 01;B313:243-7.
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Animal carotenoids. 12. Chirality of asterinic acid.

Berger R , Borch G , Liaaen-Jensen S .


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The chirality of monoacetylenic asterinic acid [(3S,3''S)-7,8-didehydroastaxanthin, 1a] has been established by NaBH4-reduction and hydrolysis of the corresponding diesters 1b and 1c providing the tetrol 9 and CD-correlation with diatoxanthin [3R,3''R)-7,8-didehydro-beta, beta-carotene-3,3''-diol, 10]. Diacetylenic asterinic acid [3S,3''S)-7,8,7'',8''-tetradehydro-beta, beta-carotene-3,3''-diol, 2a] was assigned the some absolute configuration by similar conversion to the diacetylenic tetrol 11 and CD-correlation with alloxanthin [3R,3''R)-7,8,7'',8''-tetradehydro-beta, beta-carotene-3,3''-diol, 12]. IR and CD properties of the diacetates 1C and 2C of the naturally occurring alpha-ketols are reported.

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