Naturalproductman’s Blog

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Archive for September, 2010

Chamobtusin Synthesis

Posted by naturalproductman on September 29, 2010

Hidenori Watanabe and co-workers from the University of Tokyo have published on an aza-Michael reaction approach to synthesizing chamobtusin.

chamobtusin

OL paper

Posted in Aza-Michael, Cascade Reactions, Methodology, Named Reactions | Leave a Comment »

Gold Catalyzed Three Component Approach

Posted by naturalproductman on September 29, 2010

Dean Toste and co-workers have published in Organic Letters on a gold catalyzed three component coupling reaction between an alkene, alcohol and and an aryl trimethyl silane.  A similar reaction was reported by Christopher Russell’s group from the University of Bristol.

aryl coupling

similar

OL paper (Toste)

OL paper (Russell)

Posted in C-H activation, Cascade Reactions, Gold, Methodology, Multi-Component Coupling, Transition Metal | Leave a Comment »

Synthesis of Streptolydigin

Posted by naturalproductman on September 29, 2010

Sergey Kozmin and co-worker from the University of Chicago have published in JACS on the total synthesis of streptolydigin.

streptolydigin

JACS paper

Posted in Antibiotics, Cascade Reactions, Dieckmann condensation, Horner-Wadsworth-Emmons olefination, Methodology, Named Reactions, Polyenes, Spirocycles, Spiroketals | Leave a Comment »

Azonazine

Posted by naturalproductman on September 28, 2010

Phillip Crews and co-workers have isolated an alkaloid, azonazine, that had an IC50 value of 8.37 micromolar against NF-κB luciferase.

azonazine


OL paper

Posted in Alkaloids | Leave a Comment »

Asymmetric [3+2] Reaction

Posted by naturalproductman on September 27, 2010

Interestingly, this report by Sarah Reisman and co-workers of a [3+2] cycloaddition reaction can be also seen as a Michael-Mannich reaction.

3+2

JACS paper

Posted in Asymmetric, Cascade Reactions, Methodology, Ring forming | Leave a Comment »

Lycoflexine Synthesis

Posted by naturalproductman on September 25, 2010

Johann Mulzer and co-workers at the University of Vienna have published in JACS on a total synthesis of lycoflexine where the key reaction is an enynene ring closing metathesis reaction.

enynene

JACS paper

Posted in Alkaloids, Cascade Reactions, Mannich, Metathesis, Methodology, Named Reactions, Ring forming, Ruthenium, Transition Metal | Leave a Comment »

Esculeoside A

Posted by naturalproductman on September 24, 2010

Toshihiro Nohara and co-workers at Sojo University have published in the Journal of Natural Products on the isolation of a compound that may help prevent atherosclerosis by inhibiting acyl-CoA:cholesterol acyl transferase (ACAT) or “CE” accumulation (cholesterol ester accumulation) at high doses (~50 micromolar – 40% CE accumulation inhibition).  Although the compound, esculeogenin A, was not as effective as the synthetic compound CI976, which inhibited CE accumulation by 90% at 5 micromolar, it was important to point out that the compound is from a natural food source.

esculeoside

JNP paper

Posted in Steroids, Triterpenoids | Leave a Comment »

Strychnine Synthesis

Posted by naturalproductman on September 23, 2010

No matter when the generation, a total synthesis of strychnine would always be fascinating.

strychnine

ACIEE paper

Posted in Alkaloids, Cascade Reactions, Methodology, Radical Chemistry, Ring forming | Leave a Comment »

[4+4] Photocycloaddition Reaction

Posted by naturalproductman on September 21, 2010

Scott Sieburth and co-workers from Temple University have published in Organic Letters on a [4+4] photocycloaddition reaction to access a 5,5,5,5-fused ring system.

4+4

OL paper

Posted in Cascade Reactions, Cycloaddition, Light Mediated, Methodology, Pericyclic reactions, Ring forming | Leave a Comment »

Perophoramidine Synthesis

Posted by naturalproductman on September 21, 2010

Yong Qin and co-workers from Sichuan University have published in JACS on the total synthesis of perophoramidine.  The key step was a superstoichiometric silver mediated Diels-Alder reaction.

perophoramidine

JACS paper

Posted in Alkaloids, Diels-Alder, Methodology, Named Reactions, Silver, Transition Metal | Leave a Comment »

 
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