TOTAL SYNTHESIS OF (-)-ZEPHYRANTHINE

Stereoselective total synthesis of (-)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (-)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.