Total Synthesis of (±)-2-Pupukeanone |
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Authors: | Georg Frter Jean Wenger |
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Institution: | Georg Fráter,Jean Wenger |
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Abstract: | (±)-2-Pupukenone ( 4 ) has been synthesized, the key step being the intramolcular Diels-Alder reaction of the intermediate 13 to 14 (42%) and 15 (14%). The bromodiene 12 has been obtained from the reaction of α-isopropylidene-γ-lactone (Scheme 2) 12 with sodium phenylselenide and subsequent esterification to 9 , oxidation and thermal elimination of which furnished 10 . Reduction of 10 with diisobutylaluminimum hydride and treatment of the resulting alcohol 11 with PBr3 led to the required bromodiene 12 . Finally, hydrogenation of the 14 on Pt(C) in CH3OH gave a 4:1 mixture of 2-pupukeanone ( 4 ) and epi-2-pupukeanone 16 . |
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