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Archive for the ‘Tetrahydrofuran’ Category

Laurenidificin synthesis

Posted by naturalproductman on February 3, 2016

Shoji Kobayashi and co-workers from Osaka Institute of Technology have reported in JOC on the synthesis of laurenidificin.

 

JOC paper

Posted in Tetrahydrofuran, Total Synthesis | Leave a Comment »

Inostamycin A synthesis

Posted by naturalproductman on January 22, 2016

Sung Ho Kang and co-workers from KAIST have reported in ACIE on the synthesis of inostamycin A using lanthanum (LaCl3) to effect a transmetallation of an organolithium to organolanthanum compound, which adds onto a ketone.

 

ACIE paper

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

Crystalline Sponge Method to Determine Absolute Configuration

Posted by naturalproductman on January 19, 2016

X-ray crystallography is usually a good method to determine the relative configuration of natural products (i.e. diastereomers) containing more than one stereocenter. However, the method of determining the absolute configuration of natural products is very difficult by just using X-ray crystallography. Here’s a paper from the labs of Sylvia Urban (RMIT University) and Makoto Fujita (University of Tokyo)  that reports on the use of the crystalline sponge method to determine the absolute stereochemistry of elatenyne.

 

ACIE paper 

 

Other ways to determine absolute configuration by X-ray crystallography include derivatization with a chiral reagent then crystallizing, using the effects of anomalous dispersion (Friedif values).

Posted in Asymmetric, New Techniques, Tetrahydrofuran | Leave a Comment »

Teurilene through epoxide ring opening

Posted by naturalproductman on February 22, 2013

Tomas Martin and co-workers from the Universidad de La Laguna in Spain have reported in ACIE on the synthesis of teurilene through an epoxide ring opening cascade.

epoxide

ACIE paper

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

Heronapyrrole C synthesis

Posted by naturalproductman on July 20, 2012

Christian Stark and colleague at the Universitat Hamburg have reported in Organic Letters on the synthesis of heronapyrrole C.

heronapyrrole C

OL paper

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

Shi epoxidation approach for glabrescol

Posted by naturalproductman on July 20, 2012

Jin Qu and co-workers from Nankai University have reported in Organic Letters on a synthesis of a polytetrahydrofuranyl compound using Shi epoxidation of a polyolefin intermediate.

cascade

OL paper

Posted in Asymmetric, Cascade Reactions, Methodology, Named Reactions, Polyenes, Shi epoxidation, Tetrahydrofuran, Total Synthesis | Leave a Comment »

2 routes for elatenyne and is DFT going to be a standard for natural product structure assignment?

Posted by naturalproductman on July 3, 2012

Deukjoon Kim (Seoul National University) and Jonathon Burton (University of Oxford) and co-workers have reported in JACS on a synthesis of elatenyne.

elatenyne

JACS paper

Posted in Cascade Reactions, Methodology, Tetrahydrofuran, [2+2] | Leave a Comment »

IKD-8344 synthesis

Posted by naturalproductman on April 11, 2012

Yikang Wu and co-worker from Shanghai Institute of Organic Chemistry have reported in ACIE on a synthesis of a natural product containing tetrahydrofurans, IKD-8344.

tetrahydrofuran

ACIE paper

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

Access to bis-THF rings

Posted by naturalproductman on February 8, 2012

Hiromichi Fujioka and co-workers at Osaka University have reported in Organic Letters on a method to synthesize bis-tetrahydrofurans from a diol.

iodonium
OL paper

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

Cytotoxic acetogenins

Posted by naturalproductman on November 10, 2011

Xiang Li and co-workers from Nanjing University of Chinese Medicine have isolated some bistetrahydrofurans.

bis tetrahydrofuran

JNP paper

Posted in Acetogenins, Cancer, Tetrahydrofuran | Leave a Comment »

 
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