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).

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Chapter1: Chemical Foundations
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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).
N.
1
H
H.
O.
ווח
.ווי1י
Transcribed Image Text: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). N. 1 H H. O. ווח .ווי1י
OH
H.
6.
(-)-Strychnine
* T
工n
Transcribed Image Text:OH H. 6. (-)-Strychnine * T 工n
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