138052-86-5Relevant academic research and scientific papers
Preparation of fluoroalkenes via the Shapiro reaction: Direct access to fluorinated peptidomimetics
Yang, Ming-Hsiu,Matikonda, Siddharth S.,Altman, Ryan A.
supporting information, p. 3894 - 3897 (2013/09/02)
Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.
Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine
Zhao, Shengyin,Jeon, Heung-Bae,Nadkarni, Durgesh V.,Sayre, Lawrence M.
, p. 6361 - 6369 (2007/10/03)
We report that 1-benzyl-2-methyl-3-piperidone, conveniently prepared from 3-hydroxy-2-methylpyridine, undergoes rearrangement to 1-benzyl-2-acetylpyrrolidine in aqueous 6 N HCl at reflux. Studies showing that the 2,2-dimethyl analog is inert under the same conditions support a mechanism of reversible tautomeric equilibria via ring-opened intermediates, one of which was independently synthesized and shown to be a kinetically competent intermediate to product.
The First Enantioselectice Total Syntheses of the Allopumiliotoxin A Alkaloids 267A and 339B
Goldstein, Steven W.,Overmann, Larry E.,Rabinowitz, Michael H.
, p. 1179 - 1190 (2007/10/02)
Short, highly stereocontrolled, asymmetric total syntheses of the title amphibian alkaloids are described.In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form.This short sequence proceeds in five laborato
