Palau’amine

Palau’amine, isolated by the group of the late Paul Scheuer in the University of Hawaii at Manoa in 1993, is still a desirable target for synthetic chemists around the world.  Many people are working on it and it has yet to be synthesized by anybody.  The stereochemistry of the cyclopentane core is controversial.  It is an oroidin dimer natural product just like massadine, however, massadine has been synthesized by the Baran group at Scripps last year.

JACS isolation

TTN Ring Contraction

The ring contraction reaction is a pretty neat trick using a thallium reagent published by University of Basel in Switzerland and University of Sao Paulo in Brazil by Andreas Pfaltz and Luiz Silva and co-workers in JOC.

JOC paper

A review on ring contractions by Silva can be found in TL:
TL Review

Cribrostatin 6 Synthesis

Stephen Martin (no not the actor) at the University of Texas at Austin published a paper in ACIEE on the synthesis of cribrostatin 6. The way he made the substituted aromatic ring is really cool.

ACIEE paper

A New Tetrahydrofuranyl Synthesis

Tristan Lambert at Columbia University has come up with yet another clever methodology. Using Bismuth as the catalyst, he starts with an enal and reacts with a nucleophile. The nucleophile attacks the aldehyde and a hydroalkoxylation follows. It’s a very neat and simple looking protocol.

Org. Lett.

Synthesis of (+)-Serratezamine A

Jeffrey Johnston’s group at Vanderbilt University has come up with a synthesis of serratezamine, an alkaloid with an interesting polycyclic backbone.

JACS paper

Synthesis of Norfluorocurarine

Chris Vanderwal from UC Irvine has published in JACS a synthesis of norfluorocurarine, an alkaloid with a very interesting polycyclic skeleton.

JACS paper

A New Way to Make Benzopyrans

Dean Toste at the University of California at Berkeley has recently published in JACS – you guessed it:  more gold chemistry.  This reaction takes advantage of allylic oxonium intermediates to form the new ring.  It’s certainly a puzzle to figure out this mechanism.

The JACS paper

Protonation of Vinyl Ethers for Aldol Reactions

Here’s a novel idea – using a chiral bronstead acid catalyst to promote a direct aldol reaction. Masahiro Terada at Tohoku University has recently published in JACS on this new reaction.

JACS paper

New Manzamine Alkaloids from Sponge Amphimedon sp.

Tetrahedron has some nice papers and Jun’ichi Kobayashi from Hokkaido University is one of the fine contributors to this journal.  He and his group has just recently published an isolation of some novel alkaloid structures that makes you think of nakadomarin and the like.  Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A,  and 3,4-dihydromanzamine J N-oxide are three new structures isolated from a sponge. Zamamidine had microgram/mL activity against Trypanosoma brucei, the protist that is the cause of African sleeping sickness (transmitted by the tse tse fly).

 

The TL paper

[2+2+2] Cycloaddition Strategy Catalyzed by Rh to Synthesize an Indolizidine Alkaloid

Tomislav Rovis from Colorado State has a really neat reaction out in ACIEE.  Figuring out the mechanism would be a cool thing to do – it’s not straight forward.

ACIEE paper