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Archive for the ‘Friedel-Crafts’ Category

DYKAT

Posted by naturalproductman on May 9, 2013

Jeffrey Johnson and co-workers at UNC have reported in Org Lett on a dynamic kinetic resolution.

KR

OL paper

Posted in Asymmetric, Friedel-Crafts, Kinetic resolution, Methodology, Named Reactions | Leave a Comment »

Aspidospermidine from cyclobutanone

Posted by naturalproductman on November 27, 2012

Jun’ichi Matsuo and co-workers from Kanazawa University have reported in ACIE on the synthesis of aspidospermidine.

cyclobutanone

ACIE paper

Posted in Alkaloids, Cascade Reactions, Friedel-Crafts, Methodology, Named Reactions, Total Synthesis | Leave a Comment »

Friedel-Crafts cascade

Posted by naturalproductman on April 4, 2012

Arun Ghosh and co-workers from Purdue have reported in Organic Letters on a Friedel-Crafts cascade to form a seven membered ring.
seven

OL paper

Posted in Carbene, Cascade Reactions, Friedel-Crafts, Methodology, Named Reactions, Seven-Membered Rings, Titanium, Transition Metal | Leave a Comment »

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 Friedel-Crafts

Posted by naturalproductman on June 5, 2011

Shu-Li You and co-workers from the Shanghai Institute of Organic Chemistry have reported in Synlett on an asymmetric intramolecular Friedel-Crafts alkylation.

Fridel

Synlett paper

Posted in Asymmetric, Cascade Reactions, Friedel-Crafts, Methodology, Michael, Named Reactions, Organocatalytic | Leave a Comment »

Isatisine A synthesis

Posted by naturalproductman on May 24, 2011

Guanxin Liang and co-workers from Nankai University have reported  in ACIEE on their total synthesis of isatisine.

isatisine A

ACIEE paper

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

Friedel-Crafts/Prins to get haouamine

Posted by naturalproductman on May 12, 2011

Jeffrey Aube and co-workers at Kansas have reported in Organic Letters on their approach to haouamine via a Friedel Crafts/Prins sequence.

haouamine

OL paper

Posted in Alkaloids, Cascade Reactions, Friedel-Crafts, Methodology, Named Reactions, Prins | Leave a Comment »

Pyrrole or Furan leads to Nazarov or Hydride Shift

Posted by naturalproductman on February 18, 2011

Richard Eisenberg, Alison Frontier and co-workers have reported in JACS on some transformation of a divinyl ketone, which undergoes either a Nazarov cyclization or a 1,2-hydride shift followed by a Friedel Crafts depending on whether the substituent is a pyrrole or a furan, respectively.

iridium

 

JACS paper

Posted in Cascade Reactions, Electrocyclization, Friedel-Crafts, Iridium, Methodology, Named Reactions, Nazarov cyclization, Pericyclic reactions, Transition Metal | Leave a Comment »

Taiwaniaquinone Synthesis

Posted by naturalproductman on January 26, 2011

John Hartwig and co-workers at the University of Illinois have published in JACS on the total synthesis of taiwaniaquinone – the five membered ring was formed from a Friedel-Crafts reaction mediated by a Lewis acid (BF3 etherate).  The Corey-Chaykovsky epoxidation was interesting because they state that the ylide formed from the sulfoxonium reagent did not work but the sulfonium reagent worked.

taiwaniaquinone

JACS paper

Posted in Cascade Reactions, Corey-Chaykovsky, Friedel-Crafts, Methodology, Named Reactions, Ring forming | Leave a Comment »

 
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