Asymmetric total synthesis of dibenzocyclooctadiene lignan natural products |
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Authors: | Coleman Robert S Gurrala Srinivas Reddy Mitra Soumya Raao Amresh |
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Institution: | Department of Chemistry, The Ohio State University, Columbus, 43210, USA. coleman@chemistry.ohio-state.edu |
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Abstract: | structure: see text] Full details of the asymmetric total syntheses of the dibenzocyclooctadiene lignans interiotherin A, angeloylgomisin R, gomisin O, and gomisin E (epigomisin O) are presented. The syntheses were based on a unified synthetic strategy involving a novel crotylation using the Leighton auxiliary that occurred with excellent asymmetric induction (>98:2 enantiomeric ratio), a diastereoselective hydroboration/Suzuki-Miyaura coupling reaction sequence, and an atropdiastereoselective biarylcuprate coupling, both of which occurred with total (>20:1) stereocontrol. The syntheses were achieved in six to eight steps from simple aromatic precursors. |
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