Synthesis of Variecolortide

Variecolortides have been synthesized and reported by Trauner and co-workers.

ACIEE paper

Phenoxonium Ions

Thomas Pettus and co-worker at UCSB have published in JACS on a lead(IV) acetate mediated (5+2) oxidative dearomatization to access some cedranoid sesquiterpenes.

 

JACS paper

Ningalin Synthesis

Yanxing Jia and co-workers have published in Organic Letters on the synthesis of ningalin.

 

OL paper

Fischambiguines

Jimmy Orjala and co-workers at the University of Illinois in Chicago have published in Phytochemistry on the isolation of some antibacterial compounds – fishambiguine B had an MIC value of 2 micromolar against Mycobacterium tuberculosis.

Phytochemistry paper

1,3-Dipolar Cycloaddition Followed by Decarboxylation

John Ryan and co-workers at the University of Melbourne have published in Organic Letters on a reaction which involves the 1,3-dipolar cycloaddition between an anhydride and a non-stabilized ylide followed by decarboxylation.

 

OL paper

A Slick Way to Make Allenes

Jianbo Wang and co-workers at the Peking University have published in ACIEE on a nice way to make allenes – a coupling between a terminal alkyne and an N-tosylhydrazone.

ACIEE paper

Pleurocybellaziridine

First things first:  Merry Christmas!  Happy holidays!

Toshiyuki Kan and co-workers from the University of Shizuoka have published in ACIEE on the evidence of an aziridine containing amino acid in a fungus called Angel’s wing.  They did some detective work because the aziridine containing amino acid dubbed pleurocybellaziridine is not stable enough for observation.  The carboxylic acid was not stable so they derivitized the natural product to the methyl ester form, which was more stable.  They also synthesized the aziridine containing amino acid to confirm the structures through spectral data.  The aziridine was synthesized via Mitsunobu conditions.  Interestingly the carboxylic acid form is more cytotoxic (87 micromolar, strong activity) compared to the methyl ester (233 micromolar, weak activity).  Pleurocybellaziridine damages the oligodendrocytes, which makes up the myelin sheath in the brain.

ACIEE paper

Unexpected Epoxidation

Danishefsky and co-workers have published in JACS on an epoxidation of a substrate with an olefin tethered by a sulfoxide.

 

JACS paper

Neocarzinostatin

Der-Hang Chin and co-workers at National Chung Hsing University in Taiwan have published in Chemistry a European Journal on a neat carrier protein that cyclizes neocarzinostatin, an enediyne.

 

Chemistry a European Journal paper

Boekelheide Rearrangement Strategy to form Rings Intramolecularly

Daniele Andreotti and co-workers at GlaxoSmithKline in Italy have published in the European Journal of Organic Chemistry on a Boekelheide rearrangement to form nitrogen heterocycles from pyridine-N-oxides.

 

European JOC paper