Naturalproductman’s Blog

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Archive for September, 2015

Halomon synthesis

Posted by naturalproductman on September 30, 2015

Noah Burns and co-workers at Stanford have reported in JACS on some deceptively simple looking molecules.

halogen
JACS paper

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

C-N Bond formation with cobalt

Posted by naturalproductman on September 26, 2015

Sukbok Chang and colleague from KAIST have reported in ACIE on a cobalt-catalyzed amidation of arenes using dioxazolones.

C-H

ACIE paper

Posted in C-H activation, Cobalt, Methodology, Transition Metal | Leave a Comment »

Amine/Palladium dual catalysis

Posted by naturalproductman on September 26, 2015

Sanzhong Luo and co-workers from the Chinese Academy of Sciences have reported in ACIE on a dual catalysis approach to alkylate beta-keto carbonyls with allylic alcohols.

alcohol

ACIE paper

Posted in Asymmetric, Methodology, Named Reactions, Palladium, Transition Metal, Tsuji-Trost | Leave a Comment »

Ru-macho-catalyzed deuteration

Posted by naturalproductman on September 25, 2015

Chidambaran Gunanathan and colleague from NISER have reported in Organic Letters on a ruthenium catalyzed alpha-deuteration of alcohols using a ruthenium-macho catalyst in D2O.

ruthenium
OL paper

Posted in Methodology, Ruthenium, Transition Metal | Leave a Comment »

Going from a diol to a tetrahydropyran in salinomycin

Posted by naturalproductman on September 25, 2015

Peter Leadlay and co-workers from the University of Cambridge have reported in ACIE on the enzyme that makes the tetrahydropyran ring in salinomycin. The tetrahydropyran is proposed to come from a diol where one of the hydroxy groups is in the beta-position to a ketone and subsequently dehydrates to form an enone. The enone undergoes an intramolecular Michael reaction to form the tetrahydropyran. However, when the reaction is done in vitro with the purified enzyme, they don’t see the enone intermediate, so I wonder if it is a processive reaction; in other words, the enone forms in the enzyme active site without being released and cyclizes to the tetrahydropyran.

salinomycin

ACIE paper

Posted in Biosynthesis, Chemical Biology, Enzymes, Mechanistic, Polyketides, Tetrahydropyran | Leave a Comment »

Pallavicinin synthesis

Posted by naturalproductman on September 25, 2015

Yanxing Jia and co-workers from SIOC have reported in ACIE on a synthesis of pallavicinin.

protecting group free
ACIE paper

Posted in Palladium, Total Synthesis, Transition Metal | Leave a Comment »

Mollenynes B-E

Posted by naturalproductman on September 25, 2015

Tadeusz Molinski and co-workers have reported in JACS on the isolation and characterization of mollenynes B-E.
mollenynes
JACS paper

Posted in Alkynes, Computational, DFT, Halogenated, New Techniques, NMR, Peptides, Polyenes, Stereochemistry | Leave a Comment »

Incarviatone A synthesis

Posted by naturalproductman on September 23, 2015

Xiaoguang Lei and co-workers from Peking University have reported in JACS on the synthesis of incarviatone A.

incarviatone

JACS paper

Posted in Aromatic, Total Synthesis | Leave a Comment »

Macrolactin A synthesis

Posted by naturalproductman on September 11, 2015

Nuno Maulide and co-workers have reported in Organic Letters on a 4pi-electrocyclic ring opening strategy to form the bis-diene units found in macrolactin A.

macrolactin

OL paper

Posted in Electrocyclization, Methodology, Polyenes, Total Synthesis | Leave a Comment »

Celastrol synthesis

Posted by naturalproductman on September 11, 2015

Dionicio Siegel and co-workers at UCSD have reported in JACS on the synthesis of celstrol.

celastroid

JACS paper

Posted in Cascade Reactions, Methodology, Steroids, Total Synthesis, Triterpenoids | Leave a Comment »