| The Lawton reaction consists of a sequential SN2'/1,4-conjugate addition sequence that has significant and yet under utilized potential to generate molecular complexity. A double cyclization reaction between 2-nitro-propene pivaloate, Seebach's reagent, and appropriately functionalized substrates was developed. The reaction produces three new bonds and two new rings. We propose and give supporting evidence for a mechanism that proceeds initially through a medium sized ring formation using the Lawton reaction, followed by a transannular nitro aldol ring closure. Efforts to apply this new methodology in the syntheses of citrinadin B and cyclopiamine B are described. In addition, a novel cyclobutane Lawton reagent was prepared for a prospective synthesis of the natural product brasilamide A. The development and reactivity of this cyclobutane reagent are also described. |
