Studies toward the synthesis of (-)-anisomycin. The total synthesis of (-)-2-epi-anisomycin

Exploitation of the asymmetric electron density at the crown of the oxazolidinone [221] allowed for high diastereofacial selectivity when converting the olefin to an epoxide. Regiocontrolled fragmentation of the epoxide enabled us to introduce the three essential stereocentres of the target alkaloid (-)-anisomycin [1] both contiguously and with the correct geometry. Installation of the remaining aromatic appendage allowed us to complete the molecular skeleton of the natural product; however, the synthetic step to facilitate this addition reaction also compromised the chiral integrity of the C2 position. Whilst the desired bioactive alkaloid, (-)-anisomycin [1] was not achieved upon completion of the synthesis, construction of the rare stereoisomer, (-)-2-epi-anisomycin [274] in a 9.4% overall yield demonstrates the routes future potential to deliver (-)-anisomycin [1]. For graphics please refer to abstract in pdf