Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

• Silke Dubberke,
• Muhammad Abbas and
• Bernhard Westermann

Beilstein J. Org. Chem. 2011, 7, 421–425, doi:10.3762/bjoc.7.54

• resolution; natural products; oxidative rearrangement; pig liver esterase (PLE); trisporic acid B; Introduction The generation of chiral, non-racemic compounds bearing a stereogenic quaternary carbon centre is of great interest [1][2][3][4][5][6][7][8]. Therefore, much effort has been directed towards the

• structural features can be found in the cyclic framework of (9E)- and (9Z)-trisporic acid B ((9E)-3, (9Z)-3) and its methyl esters (9E)-4 and (9Z)-4, which are very potent fungal pheromones [16][17][18][19][20]. Both the 9E and the 9Z isomer occur naturally (Figure 1). Trisporic acids have been isolated from

• orientation would cause severe steric interaction with the 3-methyl group. In conclusion, the key intermediate R-(+)-7, which can be utilized as an enantiomerically pure starting material in Suzuki’s elegant protocol [25] towards the synthesis of racemic (9E)-trisporic acid B methyl ester (9E)-4, has been