Synthetic studies directed toward guianolides: an organoiron route to the 5,7,5 tricyclic ring system

Authors

Jayapal Reddy Gone, Marquette University
Nathaniel J Wallock, Marquette UniversityFollow
Sergey Lindeman, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

3-2009

Publisher

Elsevier

Source Publication

Tetrahedron Letters

Source ISSN

0040-4039

Abstract

A diastereoselective route to the 5,7,5-tricyclic core of the guianolides is presented. This route relies on Cope rearrangement of a divinylcyclopropane prepared by alkenyl Grignard addition to a (pentadienyl)iron(+1) cation, followed by oxidative decomplexation. An additional key reaction involves oxidative rearrangement of a 3,4-epoxy-1,7-diol to generate a γ-lactone. The relative stereochemistry of this product was established by X-ray crystallography.

Comments

Accepted version. Tetrahedron Letters, Volume 50, Issue 9. March 2009. DOI: 10.1016/j.tetlet.2008.12.051. © 2009 Elsevier. Used with permission.

Recommended Citation

Gone, Jayapal Reddy; Wallock, Nathaniel J; Lindeman, Sergey; and Donaldson, William, "Synthetic studies directed toward guianolides: an organoiron route to the 5,7,5 tricyclic ring system" (2009). Chemistry Faculty Research and Publications. 44.
https://epublications.marquette.edu/chem_fac/44