Naturalproductman’s Blog

Hey, is that a natural product?!

Intermolecular hydroamination

Posted by naturalproductman on October 29, 2014

Stephen Buchwald and colleague have reported in JACS on an asymmetric intermolecular hydroamination reaction. I personally have tried an intermolecular hydroamination using a platinum catalyst, and it failed. This protocol is hopefully a good alternative.

copper

JACS paper

Posted in Copper, Methodology, Transition Metal | Leave a Comment »

Leiodermatolide synthesis

Posted by naturalproductman on October 28, 2014

Furstner and colleagues have reported in JACS on the synthesis of leiodermatolide.

leiodermatolide

JACS paper

Posted in Cancer, P-glycoprotein, Protein Targets, Total Synthesis | Leave a Comment »

Synthesis of 6-Deoxypladienolide D, which binds to SF3B1

Posted by naturalproductman on October 28, 2014

Gregg Keaney and co-workers at H3 Biomedicine have reported in Org Lett on the synthesis of 6-deoxypladienolide D.
6-deoxypladienolide D

OL paper

Posted in Named Reactions, Polyketides, Suzuki-Miyaura, Total Synthesis | 1 Comment »

Paracaseolide A synthesis

Posted by naturalproductman on October 25, 2014

Goverdhan Mehta (University of Hyderabad) and co-workers at IIT Hyderabad have reported in Tetrahedron on the synthesis of paracaseolide A.
paracaseolide A

Tetrahedron paper

Posted in Diels-Alder, Named Reactions, Total Synthesis | Leave a Comment »

Amdigenols E and G

Posted by naturalproductman on October 25, 2014

Toshiyasu Inuzuka and co-workers from Gifu University have reported in Tetrahedron Letters on the isolation of amdigenols E and G from dinoflagellates, and they had activity against N-type Ca2+ channel opening.
amdigenols E and G

TL paper

Posted in Polyketides, Protein Targets | Leave a Comment »

Axinellamines A and B

Posted by naturalproductman on October 25, 2014

When I saw the abstract figure, I wasn’t surprised to see that this paper came from Phil Baran’s group.

axinellamines

JACS paper

Posted in Alkaloids, Methodology, Total Synthesis | Leave a Comment »

Strained alkynes are in

Posted by naturalproductman on October 25, 2014

Rick Danheiser and colleague have reported in JACS on the synthesis of an aza-cyclohexyne to do the chemistries that other people have been doing with benzynes.

alkyne

JACS paper

Posted in Diels-Alder, Methodology, Named Reactions, [2+2] | Leave a Comment »

Triphenylphosphine (oxide) removal solved!

Posted by naturalproductman on October 25, 2014

You might remember an older post on something about the difficulty in removing triphenylphosphine or triphenylphosphine oxide removal. But first, how about a brief background: why would someone use triphenylphosphine in the first place? Well I can think of several reasons:

(1) Baylis-Hilman reaction

(2) Any metal cross coupling reaction using palladium tetrakis triphenylphosphine catalyst

(3) Mitsunobu reaction

So my particular problem was using the palladium tetrakis reagent to remove an Alloc protecting group.

You can see the details of the solution in page S-104 in supporting information file. But basically in a nutshell, instead of using tetrakis, I used Pd(DBA)2 and trimethylphosphine (PMe3) as the ligand, which evaporates at 38 degrees celsius.

Posted in Methodology, Random | 2 Comments »

Haouamine B pentaacetate synthesis

Posted by naturalproductman on October 11, 2014

Hidetoshi Tokuyama and co-workers from Tohoku University have reported in ACIE on the synthesis of haouamine B pentaacetate.

haouamine B

ACIE paper

Posted in Alkaloids, Structural Reassignment, Total Synthesis | Leave a Comment »

Spinosyn A, chemoenzymatically

Posted by naturalproductman on October 11, 2014

Hung-Wen Liu and co-workers from UT Austin have reported in ACIE on the chemoenzymatic synthesis of spinosyn A.

spinosyn A

 

ACIE paper

Posted in Chemical Biology, Chemoenzymatic | Leave a Comment »

 
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