Jun. 3, 2006
: Stanford graduate student Dylan Stiles calls attention
to La Clair's work and the Rychnovsky results at his blog, Tenderbutton. (The Tenderbutton blog is now archived but can be accessed with username: tender ; password:button ).
In February of this year, a total synthesis was published by James La Clair, a massive 37-step synthesis that made my head hurt when I went through it.
This is where things
start to get a little fishy. Notice footnote 22 of the main text:
"The 1H NMR spectra for this Communication were determined by
contract services. The spectra provided in the Supporting Information
were collected by N. Voss (Berlin, Germany). The operator added the peak
for CDCl3 to the spectrum of synthetic hexacyclinol, however, this was
done incorrectly at d=7.5 ppm and against the request of the author.
Additionally, one spectrum was duplicated and a copy of the spectra for
natural 5-epi-hexacyclinol was not provided."
Huh? The operator added a solvent peak? Why would anybody do that? Modifying data is a cardinal sin in science.—Dylan Stiles, Tenderbutton