Naturalproductman’s Blog

Hey, is that a natural product?!

From a trans to cis olefin and oxidations

Posted by naturalproductman on April 14, 2016

Kenji Watanabe and co-workers from the University of Shizuoka have reported in ACIE on an enzyme system (PsoE (glutathione S-transferase) and PsoF (flavin-containing monooxygenase)) that involves glutathione conjugation of a polyolefinic natural product (presynerazol) to form a glutathione adduct intermediate, which in turn is oxidized to the sulfoxide (by flavin hydroperoxide) and eliminates to form a cis-olefin (synerazol).

 

ACIE paper

Posted in Biosynthesis, Polyketides | Leave a Comment »

Roseoflavin biosynthesis

Posted by naturalproductman on April 11, 2016

Matthias Mack and co-workers from Mannheim University have reported in ACIE on the identification of an enzyme found in the biosynthesis of roseoflavin.

 

ACIE paper

Posted in Alkaloids, Antibiotics, Biosynthesis | Leave a Comment »

(−)-Deschloromytilipin A and (−)-Danicalipin A

Posted by naturalproductman on April 8, 2016

Noah Burns and co-workers from Stanford have reported in JACS on the syntheses of (−)-deschloromytilipin A and (−)-danicalipin A.

 

JACS paper

Posted in Chlorosulpholipids, Halogenated, Lipids, Methodology, Total Synthesis | Leave a Comment »

Towards puberuline C

Posted by naturalproductman on April 8, 2016

Masayuki Inoue and co-workers reported in Chemical Science on a synthesis of the hexacycle of puberuline C.

 

Chemical Science paper

Posted in Alkaloids, Total Synthesis | Leave a Comment »

(−)-Daphenylline synthesis

Posted by naturalproductman on April 8, 2016

Tohru Fukuyama and co-workers have reported in ACIE on the synthesis of (−)-daphenylline.

 

ACIE paper

Posted in Alkaloids, Total Synthesis | Leave a Comment »

Patent review – biocatalysts

Posted by naturalproductman on April 8, 2016

David Hughes at Cidara Therapeutics reported in ORPD on a patent literature search pertaining the use of biocatalysts to effect chemical transformations. He covers some P450 mediated cyclopropanation, reductive amination, Diels-Alder (artificial enzyme), nitrilase (conversion of nitrile to carboxylic acid)  reactions all catalyzed by enzymes.

 

ORPD paper

Posted in Biocatalysis, Chemical Biology, Chemoenzymatic, Enzymatic | Leave a Comment »

Cyclopropanation ring expansion

Posted by naturalproductman on April 8, 2016

Martin Trmblay and co-workers from Infinity Pharmaceuticals have reported in Organic Process Research & Development on a scalable 6 to 7 membered ring expansion towards a hedgehog antagonist. When I looked at the structure it reminded me of cyclopamine.

 

ORPD paper

Posted in Cascade Reactions, Methodology, Ring expansion, Zinc | Leave a Comment »

Curindolizine

Posted by naturalproductman on April 7, 2016

Ren Xiang Tan and co-workers from Nanjing University have reported in the isolation of a pyrrole alkaloid, curindolizine, from fungi.

 

OL paper

Posted in Alkaloids, Anti-inflammatory, Pyrroles | Leave a Comment »

Sn2 prime on gem-Chlorofluoropropenes

Posted by naturalproductman on April 7, 2016

Jean-François Paquin and co-workers from Université Laval in Canada have reported in Organic Letters on an SN2 prime reaction of gem-chlorofluoropropenes.

Posted in Methodology, Sn2 prime | Leave a Comment »

Mannolides A-C

Posted by naturalproductman on April 7, 2016

Jian-Min Yue and co-workers from the Chinese Academy of Sciences have reported in Organic Letters on the isolation of mannolides A-C.

OL paper

Posted in Biosynthesis, Cancer, Diterpenoids | Leave a Comment »

 
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