Gentric, Lionel Goff, Xavier Le Ricard, Louis Hanna, Issam Toward the Total Synthesis of Vinigrol: Synthesis of epi-C-8-Dihydrovinigrol Two approaches to vinigrol starting from the advanced tricyclic core <b>7</b> have been explored using as key intermediates epoxide <b>12</b> and diol <b>17</b>. The preparation of the properly functionalized epoxide <b>12</b> has been achieved in a straightforward fashion. However, all attempts to prepare tertiary alcohol <b>14</b> by reductive opening of <b>12</b> failed. In alternative exploratory efforts to achieve the same goal, allylic alcohols <b>16</b> and <b>29</b> were prepared by regioselective dehydration of diol <b>17</b>. Whereas <i>endo</i>-isomer <b>16</b> was found to be reluctant to undergo catalytic hydrogenation, the <i>exo</i> counterpart <b>29</b> led to the undesired isomer affording after hydrolysis epi-C-8-dihydrovinigrol <b>32</b>. vinigrol;32.;allylic alcohols 16;dehydration;fashion;alternative;preparation;exo counterpart 29;diol 17.;isomer;hydrogenation;approach;Synthesi;reductive;opening;intermediates epoxide 12;undesired;effort;Vinigrol;tricyclic core 7;hydrolysis;Total;regioselective;functionalized epoxide 12 2009-12-18
    https://acs.figshare.com/articles/journal_contribution/Toward_the_Total_Synthesis_of_Vinigrol_Synthesis_of_epi_C_8_Dihydrovinigrol/2805433
10.1021/jo901971f.s005