Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for May, 2015

Sn2 prime with trichloroacetimidates

Posted by naturalproductman on May 28, 2015

At first look of the abstract figure I thought this was an Overman rearrangement paper but no, trichloroacetimidates are also good leaving groups for Sn2 prime reactions.

Sn2 prime

ACIE paper

Posted in Cascade Reactions, Methodology, Ring forming, Sn2 prime | Leave a Comment »

Syn-1,3-carbonate access

Posted by naturalproductman on May 28, 2015

Matthew Gaunt and colleague at the University of Cambridge have reported in ACIE on a method for the synthesis of syn-1,3-carbonates.

Cu

ACIE paper

Posted in Copper, Hypervalent Iodine, Methodology, Transition Metal | Leave a Comment »

Hofmann–Löffler-Freytag Reaction

Posted by naturalproductman on May 28, 2015

Kilian Muñiz and colleague at ICIQ have reported in ACIE on an iodine catalyzed Hofmann–Löffler-Freytag reaction.

iodine

ACIE paper

Posted in Hofmann–Löffler–Freytag-type, Methodology, Named Reactions | Leave a Comment »

Sufur ylide chemistry – intramolecular cyclopropanation

Posted by naturalproductman on May 28, 2015

Nuno Maulide and co-workers from the University of Vienna have reported in JOC on an intramolecular cyclopropanation from a sulfur slide precursor and what follows is a nice mechanistic investigation.

sulfur

JOC paper

Posted in Computational, DFT, Gold, Mechanistic, Methodology, Transition Metal | Leave a Comment »

Synthesis of Paclitaxel exploiting new ways

Posted by naturalproductman on May 28, 2015

Noritaka Chida and co-workers from Keio University have reported in Organic Letters on a radical cyclization approach toward taxol.

taxol

OL paper

They access the oxetane ring via intramolecular mesylate displacement.

OL paper2

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

Brevisin via epoxide ring opening

Posted by naturalproductman on May 28, 2015

Timothy Jamison and co-workers have reported in JACS on their formal synthesis of brevisin.

polyepoxide

JACS paper

Posted in Cascade Reactions, Formal Synthesis, Rhodium, Total Synthesis, Transition Metal | Leave a Comment »

Sigillin A

Posted by naturalproductman on May 13, 2015

Stefan Schulz and co-workers at TU Braunschweig have reported in ACIE on the isolation of a polychlorinated natural product from the snow flea.

There’s a typo in the description of the article: ” in which α-vinylation of a lactone and ring-closing metathesis are they key steps.” should be “are the key steps.”
chlorine
ACIE paper

Posted in Halogenated | Leave a Comment »

Towards halichondrins

Posted by naturalproductman on May 12, 2015

I would call the vinyl halide coupling reaction with an aldehyde using chromium/nickel combination a Nozaki Hiyama Kishi coupling, but maybe because the author is one of the people in the named reaction, it wasn’t mentioned in the paper as the “NHK reaction”, but rather, a Ni/Cr-mediated reaction.

halichondrin

JACS paper

JACS paper 2

Posted in Chromium, cross coupling, Methodology, Named Reactions, Nickel, Polyketides, Total Synthesis | Leave a Comment »

HIV integrase inhibitor synthesis

Posted by naturalproductman on May 12, 2015

Chris Senanayake and co-workers from Boehringer-Ingelheim have reported in ACIE on the synthesis of

HIV

ACIE paper

Posted in Diseases, HIV, Total Synthesis | Leave a Comment »

Sarain A synthesis

Posted by naturalproductman on May 12, 2015

Tohru Fukuyama and co-workers at Nagoya University and the University of Tokyo have reported in ACIE on a formal synthesis of sarain A.

sarain

ACIE paper

Posted in Alkaloids, Total Synthesis | Leave a Comment »