Naturalproductman’s Blog

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Archive for April, 2009

Dibromophakellin Synthesis

Posted by naturalproductman on April 28, 2009

Kazuo Nagasawa’s group at the Tokyo University of Agriculture has accomplished an enantioselective total synthesis of dibromophakellin, which utilizes an Overman rearrangement to form the final ring containing a nitrogen heteroatom.


ACIEE link

Posted in Alkaloids | Leave a Comment »

Acutimine Synthesis

Posted by naturalproductman on April 28, 2009

Steven Castle at Brigham Young University in Utah has come up with a neat route to access acutimine, which possesses selective T-cell activity and anti-amnesic properties.  This comp0und is a challenging polycyclic alkaloid and the synthesis was just as impressive with a neat oxycope rearrangement, hydroamination and the use of BCl3 to promote a michael reaction in situ.  Castle’s synthesis is an amazing accomplishment and he has even beat Sorensen from Princeton to it. You can check Castle’s synthesis out in JACS.

acutimine synthesis

JACS link

Posted in Alkaloids | Leave a Comment »

SAR studies on Type II Diabetes Treatment

Posted by naturalproductman on April 26, 2009

B. Mario Pinto from Simon Fraser University in British Columbia, Canada has published a full article in JACS on some glycosidase inhibitors, which were isolated from a plant (Salacia reticulata) and all have a common five membered sulfonium moiety.

sulfonium np

JACS link

Posted in Sulfonium | Leave a Comment »

Carbocyclic Formation via Intramolecular Displacement

Posted by naturalproductman on April 26, 2009

Derrick L. J. Clive at the University of Alberta in Canada has published in JACS recently on a methodology paper that forms a bicyclic structure that is remniscent of the CP molecules that Chuo Chen had synthesized during his graduate career with Professor Matthew Shair at Harvard.  Basically it’s an SN2 prime type reaction where the enolate formed, displaces an acetate leaving group to form a carbon carbon bond.

carbocyclic formation

JACS paper

alternative product

However, the paper suggests that when DBU is used, the nitrogen base does the conjugate addition – a true SN2 prime reaction – onto the beta-position of the alpha,beta-unsaturated ester and then the tautamer of the beta-ketoester does a conjugate addition onto the side chain to kick off DBU.

Posted in Alkaloids, Methodology, Ring forming, Sn2 prime | Leave a Comment »

Chlorosulpholipid Cytotoxin Synthesis

Posted by naturalproductman on April 24, 2009

Carreira at ETH Zurich in Switzerland has come up with a synthetic plan to make a chlorosulpholipid marine cytotoxin, which is known to cause seafood poisoning.  This synthesis was published in Nature of this year.

carreira's synthesis

Nature paper

Posted in Chlorosulpholipids | Leave a Comment »

Synthesis of Agelstatin

Posted by naturalproductman on April 24, 2009

Justin Du Bois at Stanford University has come up with a new alkaloid synthesis utilizing his methodology with nitrenes.  You can find this paper in Angewandte.

dubois' synthesis

ACIEE paper

Posted in Alkaloids, Methodology, Ring forming, Transition Metal | Leave a Comment »

A Triterpenoid

Posted by naturalproductman on April 16, 2009

Morolic acid, isolated in 1950 and published in JACS by D. H. R. Barton in Harvard, is a triterpenoid that has very appealing activity.

JACS paper
It was also studied by Rios et. al at the Universidad autonoma del estado de Morales in Mexico.


Posted in Triterpenoids | Leave a Comment »

Beta-Hydroxy Ketone Synthesis

Posted by naturalproductman on April 15, 2009

This JOC article from Fernandez-Mateo’s group in the Universidad de Salamanca in Spain is a neat way to open epoxides on the more hindered end and adding nucleophiles.

epoxide opening

JOC link

Posted in Methodology, Ring Opening, Transition Metal | Leave a Comment »

Diels-Alder Reaction with Furan as the Dienophile

Posted by naturalproductman on April 15, 2009

Halenaquinone was the natural product that inspired Hideo Nemoto’s group at the Toyama Medical and Pharmaceutical University in Japan to make these furan fused quniones to act as antiviral agents.  Their method is really neat how they converted the cyano-benzocyclobutenes to the diene for the diels alder reaction.

diels alder reaction

diels alder

JOC link

This paper was highlighted in a review in Angewandte Chemie International English Edition:

ACIEE paper

Posted in Cascade Reactions, Cycloaddition, Methodology, Ring expansion, Ring forming, Unnatural Products | Leave a Comment »

Advice for Graduate School

Posted by naturalproductman on April 14, 2009

Here’s some good links to advice for graduate school:


PhD survey link

Science magazine link

ACS advice link

(If ACS link didn’t work) ‘s take on higher education

Asking for a letter of recommendation

University of Oxford’s admission criteria for undergrads but also applies to graduate students

Basically these websites let you know about a career choice in science and what it will take. Your advisor most of all is probably the most important aspect about grad school. He can make your life miserable. So I would say that this is something you must contemplate carefully before actually deciding. I would:

1) Listen carefully to the gossip going around within the department about a specific professor.

2) Be wary of professors who say one thing and act differently.

3) If something is too good to be true, it probably is – no group is going to be too happy – for example, I remember the students within the group were pretending to be SOOO happy in the group when it really was just a way for them to get you to join.

4) When professors fight for students, it’s a sign of a bad department.

5) When a professor is REALLY REALLY desperate for you to join his group, that’s a really really bad sign.

6) Also look at what former students are doing now – when most of the students go into faculty positions, usually it means that the professor is really good and that they care about their students.

7) Does the advisor let his/her students review manuscripts?  This is an essential skill when joining academics.

8) Does the advisor promote going to conferences and giving talks to practice public speaking?

9) Because of the rise in technology, we now have access to websites such as rate my professors where you can see other people’s views of the professors.  Usually this rating system can be a good sign of how good of a teacher your potential advisor will be.

(10) How well will the advisor take in the students’ input? In other words, sometimes the professor will never allow the student to have any input in the project (ie: tell the student that the ideas will never work).

(11) Will the professor let the students write their own papers?  Learning how to write is an essential skill for any scientist.

If anybody else has any other advice, it would be appreciated.

Be prepared for the worst in grad school:

Daily Nebraskan Article

Posted in Random | 5 Comments »