*Note* Click on the citations for links to the articles mentioned
Original Reference from HTML Article:
Barton, D. H. R.; O’Brian, R. E.; Sternhell, S. J. Chem. Soc. 1962, 470–478.
Published in 1962, the above article is the first to detail the procedure for hydrazone iodination. This reaction is occasionally referred to as the Barton vinyl iodide synthesis, named for the first author of this paper, Derek Harold Richard Barton, a Nobel Prize laureate. In this specific organic reaction, a hydrazone is transformed into a vinyl iodide through a mechanism involving iodine and a non- nucleophilic base such as triethylamine. The article is relevant to the synthesis of molecule 101 from molecule 22 because after molecule 22 is converted to a hydrazone by hydrazine, this hydrazone intermediate is reacted into a vinyl iodide, which is then used to generate molecule 101 through the Stille cross-coupling reaction. The reaction scheme proposed in the article is provided below. Because we are reacting under basic conditions, a strong acid will not exist in solution. Therefore, the iodine atom leaves as an anion and the protons are captured by the triethylamine. Here, the hydrazone is oxidized by iodine to produce a diazo intermediate. Next, the iodine acts as the nucleophile, attacking the diazo carbon atom. This encourages the displacement of nitrogen gas, generating a carbocation intermediate. An elimination reaction then results in the vinyl iodide.
Citation for 1st paper that has Cited Original Reference:
Szánti-Pintér, E.; Csók, Z.; Berente, Z.; Kollár, L.; Skoda-Földes, R. Steroids 2013, 78, 1177-1182.
This journal article describes the synthesis of 13α -18-nor-16-carboxamido steroids from corresponding vinyl iodides through a palladium-catalyzed aminocarbonylation reaction. 13α -18-nor-16-carboxamido steroids possess different configurations than their natural 13β analogues and as a result, may have altered biological activity and potential as pharmaceutical drugs. The Barton vinyl iodide procedure was used to generate the vinyl iodides used for this synthesis.Citation for 2nd paper that has Cited Original Reference:
Han, J.-C.; Liu, L.-Z.; Li, C.-C.; Yang, Z. Chem. Asian. J. 2013, 8, 1972-1975.
This journal article proposes an asymmetric and protecting-group-free synthesis of (+)-caribenol A. (+)-caribenol A displays inhibitory behavior toward Mycobacterium tuberculosis, the bacteria responsible for tuberculosis. The Barton vinyl iodide procedure is employed during one of the steps to synthesis (+)-caribenol A.Citation for 3rd paper that has Cited Original Reference:
Hale, K. J. Org. Lett. 2013, 15, 3181-3198.
This journal article is a Virtual Issue, a highlight of exceptional achievements in organic chemistry and how they are relevant to the world today. This particular Virtual Issue focuses on the synthesis of terpenoid- and shikimate-derived natural products, which are biologically interesting as well as structurally challenging compounds to synthesis. One of the papers mentioned is this article is the original paper for the Barton vinyl iodide procedure.