Synthesis of neodysiherbaine

The stereocontrolled synthesis of neodysiherbaine from diacetyl-l-arabinal is described. Key steps in the synthesis include the use of an asymmetric phase-transfer catalyzed glycine imine alkylation to introduce the α-amino acid function, and the RuO4-mediated oxidative cyclization of a 1,5-diene to generate the 2,7-dioxabicyclo[4.3.0]nonane ring system.