Concise stereocontrolled synthesis of keto-alcohols

ORGN 607

Partha Ghosh and Lawrence J. Williams. Department of Chemistry and Chemical Biology, Rutgers University, 610 Taylor road, Piscataway, NJ 08854
The highly functionalized structural motifs common to complex natural products continue to inspire the development of new reactions and methodologies. Substituted alpha-hydroxy ketones represent a prevalent motif among natural products. For example the epoxymicins and amphidinolides contain alpha-hydroxy ketones or there derivatives. In the course of our studies in natural product total synthesis, we demonstrated that this structural array can be accessed in a concise, stereocontroled manner. Herein we report these findings exemplified by the three step transformation shown below.