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Pharmacology
Organicrxns
 Zoapatanol:-
 Zoapatanol is a biologicallyactive moleculethat occurs naturally in the zeopatle plant, which has been used in Mexico to make a tea that can induce menstruation and labor. In 1981, Vinayak Kane and Donald Doyle reported a
synthesis of zoapatanol.Theyused the Baeyer–Villiger oxidationto make a lactone that served as a crucial buildingblock that ultimatelyled to the synthesis of zoapatanol.


 Steroids:-
 In 2013, Alina Świzdor reported the transformationof the steroid dehydroepiandrosterone to anticancer agent testololactone by use of a Baeyer–Villigeroxidation induced by fungus that produces Baeyer-Villiger
monooxygenases.



 Świzdor reported that a Baeyer-Villiger monooxygenase could change dehydroepiandrosteroneinto testololactone.

 Shapiro reaction:-TheShapiro reaction or tosylhydrazonedecomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of
organolithium reagent. The reaction was discovered by Robert H. Shapiro in 1967. The Shapiro reaction was used in the Nicolaou Taxol total synthesis.This reaction is very similar to the Bamford–Stevens reaction, which also
involves the basic decomposition of tosyl hydrazones.




 An application of the Shapiro reaction in total synthesis:-
 The Shapiro reaction has been used to generate olefins towards to complex natural products. K. Mori and coworkers wanted to determine the absolute configurationof the phytocassane group of a class of natural products
called phytoalexins. This was accomplishedby preparing the naturallyoccurring (–)-phytocassane D from Wieland-Miescher ketone. On the way to (–)-phytocassane D, a tricyclicketone was subjected to Shapiro reaction
conditions to yield the cyclic alkene product.


 Veils Mayer hack reaction:-
 The Vilsmeier–Haackreaction (also called the Vilsmeier reaction)is the chemical reaction of a substituted amide with phosphorus oxychlorideand an electron-richarene to produce an aryl aldehyde or ketone . The reaction is
named after Anton Vilsmeier and Albrecht Haack.
 For example, benzanilideand dimethylaniline react with phosphorus oxychlorideto produce an unsymmetrical diaryl ketone.Similarly, anthracene is formylatedat the 9-position.The reaction of anthracene with N-
methylformanilide, also using phosphorus oxychloride,gives 9-anthracenecarboxaldehyde:


 N-Methylformanilide and anthracene and phosphorus oxychloride
 Application:-
 The Vilsmeier-Haackreaction is an organic reaction used to convert an electron rich aromaticring to an aryl aldehyde using DMF, an acid chloride, and aqueous work-up. The mechanism begins with the reaction of DMF with the
acid chloride to form an iminiumsalt known as the “Vilsmeier reagent”.

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Pharmacology.pptx

  • 2. Organicrxns  Zoapatanol:-  Zoapatanol is a biologicallyactive moleculethat occurs naturally in the zeopatle plant, which has been used in Mexico to make a tea that can induce menstruation and labor. In 1981, Vinayak Kane and Donald Doyle reported a synthesis of zoapatanol.Theyused the Baeyer–Villiger oxidationto make a lactone that served as a crucial buildingblock that ultimatelyled to the synthesis of zoapatanol.    Steroids:-  In 2013, Alina Świzdor reported the transformationof the steroid dehydroepiandrosterone to anticancer agent testololactone by use of a Baeyer–Villigeroxidation induced by fungus that produces Baeyer-Villiger monooxygenases.     Świzdor reported that a Baeyer-Villiger monooxygenase could change dehydroepiandrosteroneinto testololactone.   Shapiro reaction:-TheShapiro reaction or tosylhydrazonedecomposition is an organic reaction in which a ketone or aldehyde is converted to an alkene through an intermediate hydrazone in the presence of 2 equivalents of organolithium reagent. The reaction was discovered by Robert H. Shapiro in 1967. The Shapiro reaction was used in the Nicolaou Taxol total synthesis.This reaction is very similar to the Bamford–Stevens reaction, which also involves the basic decomposition of tosyl hydrazones.      An application of the Shapiro reaction in total synthesis:-  The Shapiro reaction has been used to generate olefins towards to complex natural products. K. Mori and coworkers wanted to determine the absolute configurationof the phytocassane group of a class of natural products called phytoalexins. This was accomplishedby preparing the naturallyoccurring (–)-phytocassane D from Wieland-Miescher ketone. On the way to (–)-phytocassane D, a tricyclicketone was subjected to Shapiro reaction conditions to yield the cyclic alkene product.    Veils Mayer hack reaction:-  The Vilsmeier–Haackreaction (also called the Vilsmeier reaction)is the chemical reaction of a substituted amide with phosphorus oxychlorideand an electron-richarene to produce an aryl aldehyde or ketone . The reaction is named after Anton Vilsmeier and Albrecht Haack.  For example, benzanilideand dimethylaniline react with phosphorus oxychlorideto produce an unsymmetrical diaryl ketone.Similarly, anthracene is formylatedat the 9-position.The reaction of anthracene with N- methylformanilide, also using phosphorus oxychloride,gives 9-anthracenecarboxaldehyde:    N-Methylformanilide and anthracene and phosphorus oxychloride  Application:-  The Vilsmeier-Haackreaction is an organic reaction used to convert an electron rich aromaticring to an aryl aldehyde using DMF, an acid chloride, and aqueous work-up. The mechanism begins with the reaction of DMF with the acid chloride to form an iminiumsalt known as the “Vilsmeier reagent”.