Synthesis of the tetracyclic nucleus of epi-Sarcophytin, and evaluation of its activity.
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We have been investigating the synthesis of (+)-Sarcophytin o (3) and correlated compounds, and also studying their possible phytotoxic activity. For the synthesis of the tetracyclic nucleus of the C-1-epimer of (+)-3, we chose the halocyclization reaction (NBS in THF/H>20) of Diels-Alder (o) cycloadduct (+)-1, producing compound (+)-2 in 81% yield. Thus (+)-2 can now be obtained in six steps from the cheap chiron (R)-(+)-pulegone in 24% overall yield.
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Sarcophytin, Diels-Alder, Phytotoxic