Carbohydrate-Based Strategy for the Synthesis of Zaragozic Acid via a Novel Lewis Acid-Mediated Reaction of an α-Acetoxy Sulfide

Thumbnail Image
Supplemental Files
Date
1995
Authors
Kraus, George
Maeda, Hiroshi
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Authors
Person
Research Projects
Organizational Units
Organizational Unit
Journal Issue
Is Version Of
Versions
Series
Department
Chemistry
Abstract

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.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry,60(1); 2-3. Doi: 10.1021/jo00106a001. Copyright 1995 American Chemical Society.

Description
Keywords
Citation
DOI
Copyright
Sun Jan 01 00:00:00 UTC 1995
Collections