Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C.
Four members of the cordiaquinone family (cordiaquinones B, C, J, and K) were synthesized on the basis of a bioinspired scenario in five to six steps from trans, trans-farnesol. As key reactions we used the acid-catalyzed cyclization of a suitable epoxy terpenoid and a Diels-Alder reaction between a diene and benzoquinone. The relative stereochemistry of cordiaquinone C is opposite to that reported in the isolation paper and is in agreement with a plausible scenario for the biosynthesis of cordiaquinones from a common (E)-configurated naphthoquinone epoxide precursor. A fast and clean methodology for the synthesis of the naturally occurring (Z)-beta-farnesene from cis-nerolidol is also reported.
Arkoudis
Elias
E
Department of Chemistry, University of Crete, Iraklion, Greece.
Stratakis
Manolis
M
D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D011809:Quinones