Naturalproductman’s Blog

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Archive for August, 2011

Hasubanan alkaloid syntheses

Posted by naturalproductman on August 31, 2011

Sarah Reisman and co-workers have reported in ACIEE on their total syntheses of some hasubanan alkaloids.  Add an “a” and it sounds like hasubanana.

You know all of this total synthesis made me start thinking how science is evolutionary – in other words, there will always be some advancement in our field and people will publish a new paper here and there from their new findings…but there’s another aspect when way back in the day it was fine to just publish a paper and if someone were to try to publish that 20 years later, they would probably have a hard time getting it accepted.

I guess what I’m getting at is:  will there one day be a step above today where all total synthesis papers will have to be accompanied by biological studies?  For the most part – all isolation papers are accompanied by bioassays of some sort so I wouldn’t be surprised if this does happen.  But then again, that would be forcing a chemist to turn into a biologist or making friends with biologists…also to quote Phil Baran from an NIH interview:  “…we get to focus on the chemistry we love to do, and then when we’re done, we let others focus on what they love to do”

hasubanan

ACIEE paper

Posted in Alkaloids, Asymmetric, Diastereoselective, Friedel-Crafts, Methodology, Named Reactions | Leave a Comment »

FL-120B’ via Friedel Crafts

Posted by naturalproductman on August 31, 2011

John Porco and co-worker at Boston University have reported in ACIEE on the synthesis of epoxykinamycin FL-120B’ with the key step being an intramolecular Friedel-Crafts acylation to form the five membered ring.

epoxy

ACIEE paper

Posted in Friedel-Crafts, Methodology, Named Reactions, Polyketides | Leave a Comment »

Asymmetric benzoyloxylation

Posted by naturalproductman on August 31, 2011

Benjamin List and co-workers at Max-Planck-Institut fur Kohlenforschung have reported in ACIEE on an asymmetric benzoyloxylation of a cyclic ketone using a cinchona derived organocatalyst.

alpha-benzoyloxylation

ACIEE paper

Posted in Alkaloids, Asymmetric, Methodology, Organocatalytic | Leave a Comment »

Decarboxylative coupling

Posted by naturalproductman on August 30, 2011

Igor Larossa and co-workers at Queen Mary University of London have reported in ACIEE on a coupling reaction between iodoarenes and substituted o-toluic acids.

coupling

ACIEE paper

Posted in cross coupling, Methodology, Palladium, Silver, Transition Metal | Leave a Comment »

Paracaseolide A

Posted by naturalproductman on August 30, 2011

Yu-Wei Guo and co-workers from the Chinese Academy of Sciences have reported in Organic Letters on the isolation of an alpha-butenolide natural product, paracaseolide A, which had an IC50 of 6.44 micromolar against CDC25B, a phosphatase enzyme.

paracaseolide A

OL paper

Posted in Cancer, CDC25B, Dimer, Enzymes, Lactones, Protein Targets, Proteins | Leave a Comment »

Maoecrystal Z synthesis

Posted by naturalproductman on August 30, 2011

Sarah Reisman and co-workers have reported in JACS on a total synthesis of maoecrystal Z featuring a samarium mediated radical redutive cyclization of a dialdehyde intermediate.

maoecrystal Z

JACS paper

 

Isolation paper in OL

Posted in breast, Cancer, Cascade Reactions, Diterpene, leukemia, Methodology, ovarian, Radical Chemistry, Titanium, Transition Metal | Leave a Comment »

Enone from ketone

Posted by naturalproductman on August 30, 2011

Shannon Stahl and colleague from Wisconsin have reported in JACS on a palladium catalyzed oxidation of a cyclic ketone into a cyclic enone.  This of course is remniscent of the Saegusa-Ito oxidation but without the extra step of making a silyl enol ether.

enone

JACS paper

Posted in Cascade Reactions, Methodology, Palladium, Transition Metal | Leave a Comment »

Metal-free C-C bond formation

Posted by naturalproductman on August 29, 2011

Min Wang and co-workers at Shanghai Institute of Organic Chemistry have reported in Organic Letters on a TBHP promoted carbon-carbon bond formation between an azole and either an alcohol or ether.

C-C

OL paper

Posted in C-H activation, Cascade Reactions, Methodology | Leave a Comment »

MCC using gallium

Posted by naturalproductman on August 29, 2011

Akio Baba and co-workers have reported in Chemistry a European Journal on a multi-component coupling reaction that involves the coupling between a silyl ketene acetal, alkyne and GaBr3 followed by a Pd-catalyzed cross coupling with an aryl iodide.

gallium

Chemistry a European Journal paper

Posted in Cascade Reactions, Methodology, Multi-Component Coupling, Palladium, Transition Metal | Leave a Comment »

Resolve this

Posted by naturalproductman on August 29, 2011

Vladimir Birman and co-workers from Washington University in Missouri have reported in Chemistry a European Journal on a kinetic resolution of alpha-substituted alkanoic acids (the substituent includes halogens and alkyl groups).

resolve

Chemistry a European Journal paper

Posted in Asymmetric, Kinetic resolution, Methodology | Leave a Comment »

 
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