OL's Smith Stands Up for Data Integrity

Did you know Org Lett had hired a full-time Data Analyst? I didn't.

All I can say is: What took so long?

Esteemed professor and Editor Amos Smith wrote a terse, pointed piece for OL ASAP yesterday. Titled "Data Integrity," it explores ethical conduct for article submissions in the wake of several (!!) recently uncovered instances of data manipulation. Smith doesn't pull punches:

"Even if the experimental yields and conclusions of a study are not affected, ANY manipulation of research data casts doubts on the overall integrity and validity of the work reported."

What do authors say when faced with the facts? They throw their students under the bus!

"In some of the cases that we have investigated further, the  Corresponding Author asserted that a student had edited the spectra without the Corresponding Author's knowledge. This is not an acceptable excuse!"

(Perhaps we should label these "Sezen situations.")

I highly recommend reading the whole thing, if for no other reason than the righteous feeling of good-triumphing-over-evil washing over you by the end. For those interested in alternative #chemjobs, might "Data Analyst" be a pretty good use of your lab skillz?

For Your Consideration...

A New, Improved 47-Step Synthesis of Shootmenowicene

Editor: We originally sent a 1600 x 1200
color abstract. Just picture a 15-member
macrolide, densely functionalized with
heterocycles, five stereocenters,
 and chelated iron.

Abstract: Shootmenowicene, a heterocycle-containing polyketide macrolide polyene siderophore, was originally isolated in 0.009% from immature sprouts of the Bungus bungus tree. We report herein a significantly shortened 47-step route to the natural product (down from 48), which we believe will allow for kilo-scale synthesis for future clinical trials.

Synthetic highlights include: extensive use of Yamamoto's "super-silyl" protecting group, a Sezen C-H arylation / macrocyclization, kilo-scale flash-vacuum pyrolysis (FVP), and enantioselective tributyltin hydride reduction. Efforts to adapt "green" chemical considerations have been made - the penultimate oxidation occurs by swirling flask in open air for three days over twenty equivalents iron oxide catalyst.

This streamlined route utilizes seventeen silica gel purifications, four alumina plugs, two resolutions: D(-)-tartaric acid and 1R(-)-10-camphorsulfonic acid (the expensive ones, sorry!), and a one-pot global HF / Hg / chromic acid deprotection protocol. Overall yield was 0.0008%, as a mixture of diastereomers (brsm).

Two medicinally active methylated analogues will be reported in due course.

Thanks to Derek for the initial inspiration, with a gentle nudge courtesy of Chemjobber.