Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. OAc C13H15N CuCI, -Pr,NEt 2 a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-PR2NET is a base. The former can be ignored in your mechanism. b. Identify the reagents necessary for the conversion of 2 to 3.
Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here. OAc C13H15N CuCI, -Pr,NEt 2 a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-PR2NET is a base. The former can be ignored in your mechanism. b. Identify the reagents necessary for the conversion of 2 to 3.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:### Activity: Organic Synthesis Pathway
Natural products that contain the N-1,1-dimethyl-2-propenyl group often exhibit antifungal or antitumor activity. The synthesis of one such compound begins with the two steps shown here.
**Reaction Scheme:**
1. Starting Material: Compound 1 (Indole structure)
2. Intermediate: Compound 2 (product of the reaction with acetoxydimethylpropyne and base)
3. Final Product: Compound 3 (possessing the N-1,1-dimethyl-2-propenyl group)
**Reaction Steps:**
- **Step 1:**
- Reagents: Acetoxydimethylpropyne (shown with OAc leaving group), CuCl (catalyst), and i-Pr2NEt (base).
- Transformation: Compound 1 reacts to form compound 2 via an intermediate step.
- **Step 2:**
- Compound 2 is further processed to yield Compound 3.
**Structural Diagrams:**
- **Compound 1:** The structure is an indole with a secondary amine at the nitrogen position.
- **Compound 2:** This structure is derived from the reaction but needs to be drawn specifically.
- **Compound 3:** The final structure is an indole with an N-1,1-dimethyl-2-propenyl group attached to the nitrogen.
**Questions:**
**a. Draw the structure of compound 2 and show a reasonable mechanism for its formation. CuCl is used as a catalyst (behaving similarly to an acid) and i-Pr2NEt is a base. The former can be ignored in your mechanism.**
- For this task, students would need to:
- Identify the structure of Compound 2 based on its precursor (indole) and the chemical reagents provided.
- Show the steps in the mechanism, illustrating how the base i-Pr2NEt facilitates the reaction to form Compound 2.
**b. Identify the reagents necessary for the conversion of 2 to 3.**
- Here, students must determine which chemical reagents would be used to convert the intermediate Compound 2 to the final product Compound 3, highlighting the functional group transformation that takes place.
**Graph/Diagram Descriptions:**
- The reaction schematic shows linear progression from Compound 1 (starting material) to Compound 3 (final product), with an
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