The S2 Oxygen Atoms Are Essential for the Pronounced Fungitoxicity of the Sulfur-Rich Natural Product, Dysoxysulfone

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Contents Vol 58(3)

doi:10.1071/CH03253

The S₂ Oxygen Atoms Are Essential for the Pronounced Fungitoxicity of the Sulfur-Rich Natural Product, Dysoxysulfone

Sharon A. Bewick ^A, Stephen Duffy ^A, Stephen P. Fletcher ^A, Richard F. Langler ^A ^C, Heather G. Morrison ^A, Erin M. O’Brien ^A, Charles Ross ^B ^D, Vanessa C. Stephenson ^A

^A Department of Chemistry, Mount Allison University, Sackville, New Brunswick E4L 1G8, Canada.
^B Department of Structural Biology, St. Jude Children's Research Hospital, Memphis, TN 38105, USA.
^C Corresponding author (organic chemistry). Email: rlangler@mta.ca
^D Corresponding author (crystallography). Email: charles.ross@stjude.org





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Australian Journal of Chemistry 58(3) 218–223 http://dx.doi.org/10.1071/CH03253
Submitted: 22 April 2003 Accepted: 16 June 2004 Published online: 15 March 2005

Abstract

Synthesis and antifungal testing of 2,4,5,7,9-pentathiadecane 9,9-dioxide has established that the absence of oxygen atoms on S2 significantly attenuates fungitoxicity in accord with our earlier proposal. Attempts to convert that compound into dysoxysulfone led to the discovery of a novel oxidative conversion of unsymmetrical γ-sulfonyl disulfides into the corresponding symmetrical γ-sulfonyl disulfides.