Naturalproductman’s Blog

Hey, is that a natural product?!

Strictamine synthesis

Posted by naturalproductman on February 4, 2016

Jieping Zhu and co-workers reported in ACIE on the synthesis of strictamine.

 

ACIE paper

Posted in Indoles, Total Synthesis | Leave a Comment »

The enamine is formed through an oxazolidinone intermediate

Posted by naturalproductman on February 4, 2016

When I think of organocatalysis, I usually think of a carbonyl compound forming an enamine intermediate, which in turn attacks an electrophile. The enamine is usually formed when the carbonyl compound reacts with a proline-derived catalyst. By using Gaussian and experimental KIE calculations, Matthew Vetticatt and co-workers at Binghamton University reported in JACS on the way that the enamine compound is formed: through an oxazolidinone intermediate.

oxazolidinone

JACS paper

 

A review article on determining the transition state structures based on KIEs.

Posted in Computational, Isotope effects, Mechanistic | Leave a Comment »

Gold catalyzed photoredox chemistry

Posted by naturalproductman on February 3, 2016

Stephen Hashmi and co-workers have reported in ACIE on the use of a gold dimer catalyst with a diphenylphosphinomethane ligand to effect a difluoroalkylation reaction.

hashmi ACIE 2016.gif

ACIE paper

Posted in Gold, Light Mediated, Methodology, Radical Chemistry, Transition Metal | Leave a Comment »

A review of total synthesis and prospects for the future

Posted by naturalproductman on February 3, 2016

Larry Overman and co-workers have reported in ACIE on a nice review of 12 elegant examples of total synthesis of natural products bearing 2 or more quaternary carbon centers bonded to each other. I like that it is a nice “cliff notes” version of a lot of great work.

 

ACIE paper

Posted in Random, Total Synthesis | Leave a Comment »

Nahuoic acid

Posted by naturalproductman on February 3, 2016

Raymond Andersen and co-workers reported in JOC on the isolation of nahuoic acid. They used Rychnovsky’s method to determine the relative stereochemistry of the alcohols.

 

JOC paper

Posted in Cancer, Classic papers, Classical rules, Polyketides, Protein Targets, Rycnovsky's rules | Leave a Comment »

Laurenidificin synthesis

Posted by naturalproductman on February 3, 2016

Shoji Kobayashi and co-workers from Osaka Institute of Technology have reported in JOC on the synthesis of laurenidificin.

 

JOC paper

Posted in Tetrahydrofuran, Total Synthesis | Leave a Comment »

Grandilodine C synthesis

Posted by naturalproductman on February 2, 2016

Atsushi Nishida and co-workers from Chiba University have reported in ACIE on the synthesis of grandilodine C.

 

ACIE paper

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

(±)-Erythro-7′-methylcarolignan E

Posted by naturalproductman on February 2, 2016

Qiong Gu and co-workers from Sun Yat-sen University and UNC have reported in the Journal of Natural Products on the isolation of (±)-erythro-7′-methylcarolignan E with anti-HIV activity.

 

JNP paper

Posted in Diseases, HIV, Lignans | Leave a Comment »

Halicylindramides

Posted by naturalproductman on February 2, 2016

Heonjoong Kang and co-workers from Seoul National University have reported in the Journal of Natural Products on the isolation of halicylindramides (FXR antagonists).

 

JNP paper

Posted in Cancer, Depsipeptides, Protein Targets | Leave a Comment »

Tubulysin syntheses

Posted by naturalproductman on February 2, 2016

KC Nicolaou and co-workers have reported in JACS on the synthesis of tubulysin and some analogs. There are some interesting propellane analogs that reminded me of the recent Baran paper in Science that involved some strain-release amination reactions – the Baran paper involved the use of strained rings that would react with free amines to form new C-N bonds. I like the analogy in this photograph, where the two co-first authors of the paper (holding hands) represent the “strained ring” and the “amine” is Phil Baran pouring a flask to break the strain.

JACS paper

One pot C-N bond formation (Science paper):

RING STRAIN RELEASE 02.02.2016.gif

Posted in Methodology, Strained Rings, Total Synthesis | Leave a Comment »

 
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