Co-reporter:George Majetich, Thomas C. Irvin, Stephen B. Thompson
Tetrahedron Letters 2015 Volume 56(Issue 23) pp:3326-3329
Publication Date(Web):3 June 2015
DOI:10.1016/j.tetlet.2015.01.086
Alcohols undergo dehydration in a one-pot procedure when the alkoxide, formed by treating the starting alcohol dissolved in toluene with NaH, reacts with phenyl isothiocyanate and the resulting sodium carbonimidothioate salt is heated overnight at 200 °C. The phenyl isothiocyanate dehydration yields are comparable to those obtained using the classical two-step Chugaev elimination conditions.
Co-reporter:George Majetich, Ge Zou, and Shougang Hu
Organic Letters 2013 Volume 15(Issue 19) pp:4924-4927
Publication Date(Web):September 16, 2013
DOI:10.1021/ol402010r
The novel hexacyclic triterpene salvadione B was synthesized in seven steps from the chiral quinone shown. The insight gained from this synthesis permitted a two-step, one-pot sequence to introduce the three additional rings and seven chiral centers.