Animal carotenoids: 7, 8-didehydroastaxanthin and 7, 8, 7′, 8′-tetradehydroastaxanthin from lobster eggs

Synthesis of Optically Active Natural Carotenoids and Structurally Related Compounds. VIII. Synthesis of (3S,3′S)‐7,8,7′,8′‐Tetradehydroastaxanthin and (3S,3′S)‐7,8‐Didehydroastaxanthin (Asterinic Acid) The synthesis of all‐trans‐(3S,3′S)‐3,3′‐dihydroxy‐7,8, 7′,8′‐tetradehydro‐β, β‐carotene‐4,4′‐dione (1), of all‐trans‐(3S,3′S)‐3,3′‐dihydroxy‐7, 8‐didehydro‐β,β‐carotene‐4,4′‐dione (2) (asterinic acid = mixture of 1 and 2), and of their 9,9′‐di‐cis‐ and 9‐cis‐isomers is reported starting from (4′S)(2E)‐5‐(4′‐hydroxy‐2′, 6′,6′‐trimethyl‐3′‐oxo‐l′‐cyclohexenyl)‐3‐methyl‐2‐penten‐4‐ynal (8). The absolute configuration (3S,3′S) for both components 1 and 2 of asterinic acid ex Asterias rubens is confirmed on the basis of spectroscopic and direct comparison.

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Tetraterpenoids

Connolly¹,

Hill²

1991

Dictionary of Terpenoids

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Animal carotenoids: 7, 8-didehydroastaxanthin and 7, 8, 7′, 8′-tetradehydroastaxanthin from lobster eggs

Cited by 7 publications

References 8 publications

Natural Occurrence of Enantiomeric and meso‐Astaxanthin 1. Ex Lobster Eggs (Homarus gammarus)

Natural Occurrence of Enantiomeric and meso‐Astaxanthin 1. Ex Lobster Eggs (Homarus gammarus)

Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. VIII. Synthese von (3S,3′S)‐7,8,7′,8′‐Tetradehydroastaxanthin und (3S,3′S)‐7,8‐Didehydroastaxanthin (Asterinsäure)

Tetraterpenoids

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