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Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone

✍ Scribed by Andreas Bernet; Jörg Schröder; Karlheinz Seifert

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
199 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

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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