Carbohydrate-Based Strategy for the Synthesis of Zaragozic Acid via a Novel Lewis Acid-Mediated Reaction of an α-Acetoxy Sulfide
Zaragozic acid A (1) is a natural product isolated from Sporormiella intermedia and Leptodonitium elatius.' It is an important synthetic objective because it is a competitive inhibitor of squalene synthasea2 Its inhibition at the picomolar level makes it a promising candidate in the search for drugs that regulate cholesterol levels. A few synthetic approaches to the 2,8-dioxabicyclo- [3.2.lloctane skeleton have been ~ommunicated.~ As part of our continuing interest in bridged compounds,4 we sought an efficient route to a suitably functionalized bicyclic intermediate and report herein the direct synthesis of diol 2.
Reprinted (adapted) with permission from The Journal of Organic Chemistry,60(1); 2-3. Doi: 10.1021/jo00106a001. Copyright 1995 American Chemical Society.