Naturalproductman’s Blog

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Archive for May, 2011

Hypervalent iodide polycyclization

Posted by naturalproductman on May 27, 2011

Sylvain Canesi and co-workers at the Universite du Quebec have reported in Organic Letters on a polycyclization cascade initiated by a hypervalent iodide.

hypervalent iodide

OL paper

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

Bactolobin analogs

Posted by naturalproductman on May 27, 2011

Jon Clardy and co-workers at Harvard have reported in Organic Letters on the isolation of some compounds by deleting certain genes in B. thailandensis.

antibiotics

OL paper

Posted in Biosynthesis, Chemical Biology, Lactones, Peptides | Leave a Comment »

Benzyne mcr

Posted by naturalproductman on May 27, 2011

Hideto Miyabe and co-workers from Hyogo University have reported in ACIEE on a multicomponent reaction between benzynes, DMF and beta-ketoesters or 1,3-diketones to afford 2H-chromene or isocoumarin derivatives.

acetate

ACIEE paper

Posted in benzyne, Cascade Reactions, Methodology, Multi-Component Coupling | Leave a Comment »

2 rings from none

Posted by naturalproductman on May 27, 2011

Erik Alexanian and colleague have reported in ACIEE on cyclization using a rhodium catalyst to couple two allenes and an alkene…basically a [2+2+2] cycloaddition.

rhodium

ACIEE paper

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

Kainic acid from a vinyl aziridine

Posted by naturalproductman on May 27, 2011

Varinder Aggarwal and co-workers from the University of Bristol have reported in ACIEE on a [3+2] reaction between a vinyl aziridine and a Michael acceptor while taking advantage of Tsuji-Trost allylation.  Additionally, they cleaved off the phenyl group on the resulting pyrrolidine ring using a RuCl3/H5IO6/NaIO4 oxidation protocol.

palladium

ACIEE paper

Posted in C-C Bond Breaking, Cascade Reactions, Methodology, Named Reactions, Palladium, Transition Metal, Tsuji-Trost | Leave a Comment »

Copper/amine cooperative catalysis

Posted by naturalproductman on May 26, 2011

Veronique Michelet and co-workers from CNRS have reported in the European Journal of Organic Chemistry on a copper/amine cooperative catalyzed Conia-ene type reaction.

looks like

European JOC paper

Posted in Cascade Reactions, Conia-Ene, Copper, Methodology, Named Reactions, Organocatalytic, Transition Metal | Leave a Comment »

Phomopsin structure revision

Posted by naturalproductman on May 26, 2011

Shunya Takahashi and co-workers from RIKEN have reported in Organic Letters on a structural reassignment of the polyketide, phomopsin.
phomopsin

OL paper

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

Three component coupling using benzynes

Posted by naturalproductman on May 25, 2011

Hiroto Yoshida and co-worker at Hiroshima University have reported in Chem Comm on an approach to access ortho-quinone methides from benzynes and DMF.

ortho-quinone methides

Chem Comm paper

Posted in Cascade Reactions, Methodology, Multi-Component Coupling | Leave a Comment »

This molecule is pretty

Posted by naturalproductman on May 25, 2011

Keiji Tanino and co-workers from Hokkaido University have reported in Nature Chemistry on the synthesis of solanoeclepin A – this molecule is similar to glycinoeclepin in activity and structure…the biological activity is related to dafachronic acid where it stimulates the hatching of nematodes.

solanoeclepin A

Nature Chemistry paper Read the rest of this entry »

Posted in Cascade Reactions, Cycloaddition, Methodology, Pericyclic reactions, Triterpenoids | Leave a Comment »

Esulatin J

Posted by naturalproductman on May 25, 2011

Judit Hohmann and co-workers from the University of Szeged in Hungary have reported in the Journal of Natural Products on the isolation of some diterpenes including esulatin J, which had 46.8% inhibition of MCF7 cells at a concentration of 10 micrograms/mL.

diterpene

JNP paper

Posted in Cancer, Diterpene, Jatrophane | Leave a Comment »

 
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