Preparation of the Zaragozic Acid Core through Rearrangement of an Oxonium Ylide

Authors

John B. Brogan, University of New Hampshire
Charles K. Zercher, University of New HampshireFollow

Abstract

The diastereoselective formation of a 2,8-dioxabicyclo[3.2.1]octane skeleton was accomplished through the generation and rearrangement of a bicyclic oxonium ylide. The skeleton which was formed is common to the zaragozic acid family and possesses appropriate functionality for further manipulation. The study also revealed the first example of an exocyclic 2,3-shift from a acetal-derived oxonium ylide.

Department

Chemistry

Publication Date

3-26-1998

Journal Title

Tetrahedron Letters

Publisher

Elsevier

Digital Object Identifier (DOI)

10.1016/S0040-4039(98)00127-0

Document Type

Article

Recommended Citation

Preparation of the Zaragozic Acid Core through Rearrangement of an Oxonium Ylide, Brogan, J. B.; Zercher, C. K., Tetrahedron Lett. 1998, 39, 1691-1694.

Rights

Copyright © 1998, Elsevier