Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for September, 2013

Merochlorin A synthesis

Posted by naturalproductman on September 27, 2013

Jonathan George and co-workers from the University of Adelaide have reported in ACIE on the synthesis of merochlorin A.

merochlorin A

ACIE paper

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

Asperolide C synthesis

Posted by naturalproductman on September 27, 2013

Erick Carreira and co-workers have reported in ACIE on a synthesis of asperolide C using an iridium catalyzed poly-ene cascade cyclization.

Ir

ACIE paper

Posted in Asymmetric, Cascade Reactions, Iridium, Methodology, Total Synthesis, Transition Metal | Leave a Comment »

Maoecrystal V synthesis

Posted by naturalproductman on September 25, 2013

Armen Zakarian and co-workers have reported in JACS on a synthesis of maoecrystal V.

maoecrystal V

JACS paper

Posted in C-H activation, Methodology, Radical Chemistry, Total Synthesis | Leave a Comment »

SN2 type reaction of tertiary alcohols?!

Posted by naturalproductman on September 13, 2013

Ryan Shenvi and co-workers at Scripps have reported in Nature on an SN2 type reaction of tertiary alcohols displaced by isonitriles using TMSCN.

Nature paper

Posted in Methodology | Leave a Comment »

Writing manuscripts

Posted by naturalproductman on September 13, 2013

Nathan Blow wrote an editorial about how to write manuscripts.

Biotechniques paper

Posted in Random | Leave a Comment »

ET-743 synthesis

Posted by naturalproductman on September 9, 2013

Tohru Fukuyama and co-workers have reported in JACS on a synthesis of ecteinascidin 743.

ET-743

JACS paper

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

A man-made chemical structure is actually a natural product!

Posted by naturalproductman on September 6, 2013

Here’s an interesting report from ACIE: Michel De Waard and co-workers from CNRS found tramadol, a compound designed as a simplified structure of morphine to treat pain and manufactured by Grunenthal GmbH (Germany), in Nauclea latifolia Sm. (Rubiaceae) plant, also known as the African peach or pincushion plant.

Root

ACIE paper

Posted in Alkaloids | Leave a Comment »

Making HSQC look nicer

Posted by naturalproductman on September 6, 2013

Gareth Morris and co-workers at the University of Manchester and beyond have reported in ACIE on enhancing the resolution of HSQC contours. I imagine this would be useful when carbon chemical shifts and proton chemical shifts are jumbled together.

HSQC

ACIE paper

Posted in New Setups, New Types | Leave a Comment »

An alkyl shift

Posted by naturalproductman on September 6, 2013

Richmond Sarpong and co-workers have reported in ACIE on a slick alkyl shift to afford (±)-3-demethoxyerythratidinone and (±)-cocculidine.  I may be wrong but in Scheme 7 of the paper:  going from intermediates 29 to 30 to 4, there is a loss of the enantioselectivity – the scheme shows that the final product is racemic (+/-) but the precursor 29 has 99% enantiomeric excess. Hmm.

alkaloids

ACIE paper

Posted in Cascade Reactions, Methodology, Random, Total Synthesis | 2 Comments »

Minovincine synthesis

Posted by naturalproductman on September 5, 2013

David Macmillan and co-workers have reported in ACIE on a synthesis of minovincine.

minovicine

ACIE paper

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