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Archive for the ‘Methodology’ Category

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 »

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 »

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 »

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 »

Interrupted Nazarov

Posted by naturalproductman on October 7, 2014

FG West and co-workers from the University of Alberta have reported in an Nazarov cyclization study combining DFT and experiment to explain the diastereoselectivity.

 

 

JACS paper

Posted in Cascade Reactions, Methodology, Named Reactions, Nazarov cyclization | Leave a Comment »

Not just benzynes anymore: cyclohexyne and cylcopentyne

Posted by naturalproductman on October 7, 2014

Neil Garg and co-workers have reported in JACS on an annulation process involving cyclohexynes.

 

JACS paper

Posted in Cascade Reactions, Methodology | Leave a Comment »

Cascade metathesis towards humulanolides

Posted by naturalproductman on October 4, 2014

Chuang-Chuang Li and co-workers at the University of Science and Technology have reported in JACS on a cascade metathesis approach to the synthesis of humulanolides.

metathesis

JACS paper

Posted in Cascade Reactions, Humulanolides, Metathesis, Methodology | Leave a Comment »

NHC-catalyzed [4+2]

Posted by naturalproductman on October 4, 2014

David Lupton and co-worker at Monash University have reported in JACS on an NHC-catalyzed [4+2] reaction.
4+2

JACS paper

Posted in Carbene, Cascade Reactions, Methodology | Leave a Comment »

 
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