Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

Abstract

The stereoselective total synthesis of strongylodiol H and I has been accomplished. The synthetic procedure comprised the stereoselective reduction of a ketone functionality in an ene–yne–one employing CBS as a catalyst and a Cadiot–Chodkiewicz coupling reaction as the key reaction steps. A common aldehyde intermediate has been used for the synthesis of both strongylodiols.

Keywords

• alkylation
• Cadiot–Chodkiewicz coupling
• Corey–Bakshi–Shibata reduction
• Mosher’s analysis
• Wittig reaction