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Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone
Author(s) -
Bernet Andreas,
Schröder Jörg,
Seifert Karlheinz
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390158
Subject(s) - sesquiterpene , chemistry , total synthesis , aldehyde , quinone , demethylation , stereochemistry , stereoselectivity , aryl , benzoquinone , organic chemistry , alkyl , biochemistry , gene expression , dna methylation , gene , catalysis
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 CC 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.