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Archive for the ‘Biosynthesis’ Category

Anditomin biosynthesis

Posted by naturalproductman on October 4, 2014

Ikuro Abe and co-workers from the University of Tokyo have reported in JACS on a biosynthetic study of anditomin.

biosynthesis

JACS paper

Posted in Biosynthesis, Meroterpenoids | Leave a Comment »

Merochlorins A and B syntheses, enzymatically

Posted by naturalproductman on August 18, 2014

Bradley Moore and Phil Baran’s groups teamed up to synthesize merochlorin A and B.

Merochlorin

ACIE paper

Posted in Biosynthesis, Chemical Biology, Enzymatic, Polyketides, Total Synthesis | Leave a Comment »

Polyketide dimerizing P450s

Posted by naturalproductman on April 18, 2014

Michael Muller and co-workers reported in JACS on the identification of some P450 enzymes involved in dimerizing polyketide natural products.

JACS paper

Posted in Biosynthesis, Polyketides | Leave a Comment »

Fumigatoside A

Posted by naturalproductman on March 17, 2014

Someone has brought to my attention the isolation of a recent alkaloid containing a strange alkynol attached to a nitrogen.

The main supporting evidence for this structure is the 3-bond HMBC correlation of the OH proton to the alkyne carbon taken in DMSO (the alcohol is at ~9.8 ppm).  The fishy thing here is that there is no 2-bond HMBC correlation (I assume it would be two bond from O-H and C-O) from the OH to the nearest alkyne carbon.

An interesting question would be how this alkynol would be introduced in the biological system. Alkynes are usually precursors to alkynols in P450 reactions and give rise to a rearrangement to form ketenes, which inactivate the enzymes.

Synthetically, I first saw alkynol structures from Sergey Kozmin’s work back in 2006. I should say that even here they are not alkynols – they are siloxy alkynes.

Perhaps anybody else has an opinion on this interesting structure?
alkynol

OL paper

Posted in Alkaloids, Biosynthesis | 2 Comments »

Fluorinated compounds, biosynthetically

Posted by naturalproductman on September 5, 2013

Michelle Chang and co-workers at Berkeley have reported in Science on a way to access fluorinated natural products using fluoroacetate as the building block.

 

Science paper

Posted in Biosynthesis, Unnatural Products | Leave a Comment »

Biosynthesis of andrastin A

Posted by naturalproductman on August 3, 2013

Ikuro Abe and co-workers from the University of Tokyo have reported in Tetrahedron on how they reconstituted the biosynthetic pathway for andrastin A in a fungus.

andrastin

Tetrahedron paper

Posted in Biosynthesis, Chemical Biology | Leave a Comment »

Multi-component approach to guajadial B

Posted by naturalproductman on November 21, 2012

Looking at this molecule, one would never think that you can mix three things, a penta-substituted benzene ring, benzaldehyde and humulene, and obtain the final compound, guajadial! Ji-Kai Liu and co-workers at the Kunming Institute of Botany did such a thing!

MCC
OL paper

Posted in Biosynthesis, Cascade Reactions, Meroterpenoids, Methodology, Multi-Component Coupling, One pot, Total Synthesis | Leave a Comment »

Baeyer-Villiger reaction in the glivocarcin and jadomycin biosynthesis

Posted by naturalproductman on October 30, 2012

Jurgen Rohr and co-workers from the University of Kentucky have reported in JACS on a Baeyer-Villiger reaction in the glivocarcin and jadomycin biosynthesis.

glivocarcin

JACS paper

Posted in Baeyer-Villiger, Biosynthesis, Named Reactions, Polyketides | Leave a Comment »

Diepoxide intermediate

Posted by naturalproductman on April 20, 2012

Hideaki Oikawa and co-workers at Hokkaido University have reported in JACS on a sequential epoxidation of a bis olefin compound to yield a diepoxide that undergoes a ring opening cascade to form two cyclic polyethers (a tetrahydropyran and tetrahydrofuran).

epoxidation

JACS paper

Posted in Biosynthesis, Carboxylic acids, Chemical Biology, Enzymatic, Methodology | Leave a Comment »

More on oroidin dimers

Posted by naturalproductman on March 30, 2012

Tadeusz Molinski and co-workers have reported in JNP on the biosynthesis study of benzoscpetrin C and nagelamide H.
oroidin

JNP paper

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

 
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