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
Elias Arkoudis
Manolis Stratakis
10.1021/jo800355y.s001
https://acs.figshare.com/articles/journal_contribution/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/2932612
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 <i>trans</i>,<i>trans</i>-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 (<i>E</i>)-configurated naphthoquinone epoxide precursor. A fast and clean methodology for the synthesis of the naturally occurring (<i>Z</i>)-β-farnesene from <i>cis</i>-nerolidol is also reported.
2008-06-20 00:00:00
Relative Stereochemistry
isolation paper
Bioinspired Approach
cordiaquinones B
bioinspired scenario
Cordiaquinone C
Cordiaquinones B
cordiaquinone family
cordiaquinone C