2. Strychnine (6) is a notorious poison for both humans and rats. The first synthesis of this molecule was achieved by R. B. Woodward over sixty years ago (JACS 1954, 76, 4749-4751). In the last step of Woodward's synthesis, compound 1 was converted into 6 via intermediates 2-5, as shown. a) Draw all curved arrows that show the entire transformation of 1 into 6, and identify the entire sequence of arrow-pushing patterns. You may draw directly on the structures provided. b) For the step in which 4 is transformed into 5, identify the nucleophilic center and the electrophilic center. This step involves the creation of a new chirality center. Determine its configuration and explain why this reaction is enantiospecific (why the other possible configuration is not observed).

2. Strychnine (6) is a notorious poison for both humans and rats. The first synthesis of this molecule was achieved by R. B. Woodward over sixty years ago (JACS 1954, 76, 4749-4751). In the last step of Woodward's synthesis, compound 1 was converted into 6 via intermediates 2-5, as shown. a) Draw all curved arrows that show the entire transformation of 1 into 6, and identify the entire sequence of arrow-pushing patterns. You may draw directly on the structures provided. b) For the step in which 4 is transformed into 5, identify the nucleophilic center and the electrophilic center. This step involves the creation of a new chirality center. Determine its configuration and explain why this reaction is enantiospecific (why the other possible configuration is not observed).

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.36P

See similar textbooks

Similar questions

Consider the following transformation below, which Prof. Ingoglia conducted during his post-doctoral research. a. Draw the product of the reaction in the box provided. b. Provide an arrow-pushing mechanism for the formation of the product you drew in part (a).
When drawing organic chemistry mechanisms with NaOCH3, do we automatically dissociate it into Na+ and OCH3-, making it easier to go through SN2 and/or E2 reactions? Does NaOCH3 dissociate, and is this why it is a strong nucleophile?
In both examples below the reactants shown are combined to bring about a nucleophilic substitution (SN1, SN2) and/or elimination (E1, E2) reaction. What is the major reaction that takes place in each case?
1.) Can you draw this out in more detail and explain the FC alkylation 2.) I do not understand what it is asking 3.) Can you confirm if it is correct or not
can you explain the steps of this mechansm
Please show the mechanisms that convert compound 1 into compound 2. Thank you!
which newman projection displays the proper antiperiplanar orientation for an E2 elimination of the reaction sequence below
Draw a detailed mechanism for the FeBr3@catalyzed reaction of ethylbenzene with bromine, and show why the sigma complex (and the transition state leading to it) is lower in energy for substitution at the ortho and para positions than it is for substitution at the meta position.
The above synthesis was designed using the Organic Chemistry Roadmaps in the appendix of your textbook. In this synthesis starting with acetylene, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound j. Use the wedge/hash bond tools to indicate stereochemistry where it exists. In cases where there is more than one answer, just draw one. Show stereochemistry in a meso compound. Do not include counter-ions, e.g., Na+, I-, in your answer.
Arrange the structure on the image with regard to the reactivity towards nucleophilic acyl substitution 1 being the least and 3 being the most
which one is more nucleophilic CH3CO2- or -OH? Does it have anything to do with resonance or bulkyness (sterically hindered)??
For SN1 Explain if 3o ( tertiary) alkyl halides reacted (fastest or slowest) explain why. Be sure to explain if alkyl halides did not react or did react and why. 3o (tertiary) compounds listed are: 2-chloro-2-methylpropane (see picture) Base your explanations on the following considerations: the nature of leaving group, the effect of structure, steric hindrance and any other feature.