Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone |
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Authors: | Andreas Bernet Jrg Schrder Karlheinz Seifert |
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Institution: | Andreas Bernet,Jörg Schröder,Karlheinz Seifert |
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Abstract: | The synthesis of the marine sesquiterpene quinone (+)‐hyatellaquinone ( 1 ) was achieved starting from the sesquiterpene aldehyde (+)‐albicanal ((+)‐ 3 ) (Schemes 3 and 4). Coupling of (+)‐albicanal with 2,3,5,6‐tetramethoxyphenyllithium led to the aryl‐sesquiterpene system, which was modified to the target molecule. Furthermore, the first total synthesis of the marine compound spongiaquinone ( 2 ) was carried out starting from ((?)‐albicanal (?)‐ 3 ) in a reaction sequence encompassing a stereoselective C?C bond hydrogenation and a one‐pot AcOH elimination/demethylation reaction (Schemes 7 and 10). The occurrence of 1,2‐ and 1,4‐benzoquinone forms of 1 and 2 depends on the pH of the solvent system. |
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