Naturalproductman’s Blog

Hey, is that a natural product?!

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 | Leave a Comment »

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 »

Hapalindole alkaoid syntheses

Posted by naturalproductman on October 11, 2014

Ang Li and co-workers from SIOC have reported in ACIE on the syntheses of hapalindole compounds.

hapalindole

ACIE paper

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

Δ9-THC synthesis

Posted by naturalproductman on October 11, 2014

Erick Carreira and co-workers have reported in ACIE on the synthesis of dehydrotetrahydrocannabinol.

THC

ACIE paper

Posted in Dual Catalysis, Methodology, Total Synthesis | Leave a Comment »

N-methylwelwitindolinone B isothiocyanate synthesis

Posted by naturalproductman on October 11, 2014

Neil Garg and co-workers reported the synthesis of N-methylwelwitindolinone B isothiocyanate in JACS.

alkaloid

JACS paper

Posted in Alkaloids, Total Synthesis | Leave a Comment »

 
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