Naturalproductman’s Blog

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Archive for May, 2010

RRM Strategy for Epihalosaline and Porantheridine

Posted by naturalproductman on May 28, 2010

Guillaume Vincent and co-workers at CNRS have published in JOC on a ring rearrangement metathesis (RRM) to access a bicyclic piperidone from a Diels-Alder adduct.  Metathesis is not just about making alkenes anymore.

metathesis

JOC paper

Posted in Alkaloids, Cascade Reactions, Metathesis, Methodology, Ring forming, Ring Opening, Ruthenium, Transition Metal | Leave a Comment »

Phalarine Synthesis

Posted by naturalproductman on May 28, 2010

Samuel Danishefsky and co-workers have published in JACS on the total synthesis of phalarine from an amino acid.

phalarine

JACS paper

Posted in Alkaloids, Cascade Reactions, Methodology, Named Reactions, Pictet-Spengler, retro-Mannich | Leave a Comment »

Pyrrothines

Posted by naturalproductman on May 28, 2010

Ahmed Lebrihi and co-workers at LPBVB in Algeria have published in the Journal of Natural Products on the isolation of new dithiopyrrolone antibiotics after adding valeric acid to Saccharothrix algeriensis culture broth.  Formylpyrrothine had an antimicrobial MIC activity of 2 micrograms/mL against Bacillus subtilis.

dithio

JNP paper

Posted in Polythio Compounds | Leave a Comment »

Gold Catalyzed Conia-ene Reaction

Posted by naturalproductman on May 28, 2010

Paul Davies and co-worker at the University of Birmingham have published in Organic and Biomolecular Chemistry on a gold catalyzed Conia-ene reaction where the presence of water was required for the reaction to occur.

water

OBC paper

Posted in Cascade Reactions, Gold, Methodology, Ring forming, Transition Metal | Leave a Comment »

Enantioselective Nazarov using a Thiourea Catalyst

Posted by naturalproductman on May 28, 2010

Marcus Tius and co-workers at the University of Hawaii have published in JACS on an organocatalytic enantioselective Nazarov reaction that uses a chiral thiourea catalyst.  The terminal ester seems necessary to activate the substrate.

thiourea

JACS paper

Posted in Cascade Reactions, Electrocyclization, Methodology, Named Reactions, Nazarov cyclization, Organocatalytic, Pericyclic reactions | Leave a Comment »

Gold Catalyzed Desymmetrization

Posted by naturalproductman on May 27, 2010

Frank Rominger and co-workers have published in Chemical Communications on a gold catalyzed desymmetrization of a dialkynyl bis furan substrate.
desymmetrization


Chem Comm paper

Posted in Cascade Reactions, Gold, Methodology, Ring forming, Transition Metal | Leave a Comment »

Bryostatin Analog Synthesis

Posted by naturalproductman on May 26, 2010

Gary Keck and co-workers at the University of Utah have published in ACIEE on the synthesis of a desoxy bryostatin analog.  They basically removed the hydroxy group on the C-9 position, which is a hydroxy group on a hemiacetal of a tetrahydropyran ring system, by treating a bis-ketal with triethylsilane and TMSOTf.  This selective reduction removed the C-9 oxygen but left in tact the C-19 oxygen.

selective deoxygenation


ACIEE paper

Posted in Methodology, Polyketides, Unnatural Products | Leave a Comment »

Another Englerin Synthesis

Posted by naturalproductman on May 26, 2010

Nicolaou and Chen and co-workers have published on a total synthesis of englerin A in JACS.

englerin

JACS paper

Posted in Achmatowicz rearrangement, Methodology, Sesquiterpenoids, Seven-Membered Rings | Leave a Comment »

Hetero-Diels-Alder

Posted by naturalproductman on May 26, 2010

Janusz Jurczak and co-workers at Polish Academy of Sciences have published in Synlett on a hetero-Diels-Alder reaction by using a chromium-Schiff base complex.

diels-alder

Synlett paper

Posted in Cascade Reactions, Chromium, Cycloaddition, Diels-Alder, Methodology, Named Reactions, Pericyclic reactions, Transition Metal | Leave a Comment »

Carboamination via Copper Acetate

Posted by naturalproductman on May 26, 2010

Majumdar and co-workers at the University of Kalyani have published in Synlett on a carboamination process catalyzed by copper acetate.

carboamination

Synlett paper

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

 
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