Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for February, 2013

Puraquinonic acid synthesis

Posted by naturalproductman on February 20, 2013

James Gleason and co-workers from McGill University have reported in ACIE on the synthesis of puraquinonic acid. I didn’t know that Robert Ireland of University of Virginia died last year.

puraquinonic acid

ACIE paper

Advertisements

Posted in Methodology, Polyketides, Total Synthesis | Leave a Comment »

Trichodermatide A synthesis

Posted by naturalproductman on February 20, 2013

Kou Hiroya and co-workers from Musashino University have reported in ACIE on the synthesis of trichodermatide A.

beast

ACIE paper

Posted in Polyketides, Total Synthesis | Leave a Comment »

Sarcophytonolide synthesis

Posted by naturalproductman on February 20, 2013

Isao Kadota and co-workers from Okayama University have reported in Org Lett on a synthesis of sarcophytonolide.

diastereomers

OL paper

Posted in Macrocycles, Methodology | Leave a Comment »

Colletoic acid synthesis

Posted by naturalproductman on February 20, 2013

Masahisa Nakada and co-worker from Waseda University have reported in Org Lett on a synthesis of colletoic acid.

synthesis

OL paper

Posted in Carboxylic acids, Spirocycles, Total Synthesis | Leave a Comment »

That’s pretty strained

Posted by naturalproductman on February 20, 2013

Fumitoshi Kakiuchi and co-workers from Keio University have reported in Org Lett on a rhodium catalyzed [2+2] reaction between a terminal alkyne and an electron deficient alkene to form a cyclobutene.

strained

OL paper

Posted in Cycloaddition, Methodology, Rhodium, Transition Metal, [2+2] | Leave a Comment »

Citreoviripyrones A and B

Posted by naturalproductman on February 20, 2013

Teigo Asai and co-workers from Tohoku University have isolated some cyclobutane containing polyketides. They also treated a linear polyketide precursor, citreovirimontanin with a palladium catalyst to form the 6,4-bicycle.

polyketide

OL paper

Posted in Polyketides, Total Synthesis | Leave a Comment »

Chlorizidine A

Posted by naturalproductman on February 20, 2013

Chambers Hughes and co-workers at Scripps have reported in Organic Letters on the isolation of chlorizidine A, which had low micromolar LC50 values against some cancer cell lines from NCI. Another interesting point in this paper is the way they assigned the chiral carbon stereocenter as S from an X-ray crystal structure of the molecule, which also incorporated a benzene molecule. They determined the stereocenter using the Flack parameter.

chlorizidine A

OL paper

Flack parameter ref (Acta Cryst)

Posted in Alkaloids, breast, Cancer, melanoma, Stereochemistry | Leave a Comment »

Cladionamide G synthesis

Posted by naturalproductman on February 20, 2013

Gregory Dake and co-workers from the University of British Columbia have reported in OL on the synthesis of cladoniamide G.

synthesis

OL paper

Posted in Alkaloids, Total Synthesis | Leave a Comment »

Aziridinone oxidant

Posted by naturalproductman on February 20, 2013

Yian Shi and co-workers have published in OL on a copper catalyzed oxidation of alcohols using an aziridinone oxidant.

copper

OL paper

Posted in Cascade Reactions, Copper, Methodology, Transition Metal | Leave a Comment »

Anion cascade

Posted by naturalproductman on February 11, 2013

Hongbin Zhai and co-workers at Lanzhou University have reported in OL on a cascade epoxide ring opening reaction.

anion

OL paper

Posted in Cascade Reactions, Methodology | Leave a Comment »