Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels--Alder/Claisen rearrangement |
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| Authors: | Tisdale Eric J Slobodov Irina Theodorakis Emmanuel A |
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| Affiliation: | Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0358, USA. |
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| Abstract: | A concise synthesis of forbesione (1) and desoxymorellin (3) is presented. Central to the strategy is a biomimetic Claisen/Diels-Alder/Claisen reaction cascade that proceeds in a regioselective manner and produces the desired scaffold exclusively. The observed regioselectivity and product distribution of the Claisen/Diels-Alder/Claisen reaction are attributed to the electronic effects of the xanthone oxygen (O10), the C9 carbonyl group and the nature of the C1 functionality. |
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