Decytospolides A and Bare fungal natural products that are toxic to some cancer cells, In a synthesis of these natural products, compound 3 was prepared via the reaction between an epoxide (compound 2) and a Grignard reagent (Tetrahedron: Asymmetry 2015. 26, 296-303). Draw the structure of 2, and provide a complete mechanism for the conversion of 1 to 3. OBn OBn NaH TsO 2) HO Bn Decytonpolide A H Decytospolide R- COCH
Decytospolides A and Bare fungal natural products that are toxic to some cancer cells, In a synthesis of these natural products, compound 3 was prepared via the reaction between an epoxide (compound 2) and a Grignard reagent (Tetrahedron: Asymmetry 2015. 26, 296-303). Draw the structure of 2, and provide a complete mechanism for the conversion of 1 to 3. OBn OBn NaH TsO 2) HO Bn Decytonpolide A H Decytospolide R- COCH
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
Chapter22: Reactions Of Benzene And Its Derivatives
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Problem 22.50P: Following is the structure of miconazole, the active antifungal agent in a number of...
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![Decytospolides A and Bare fungal natural products that are toxic to some cancer cells, In a synthesis of these natural products.
compound 3 was prepared via the reaction between an epoxide (compound 2) and a Grignard reagent (Tetrahedron: Asymmetry 2015.
26, 296-303). Draw the structure of 2, and provide a complete mechanism for the conversion of 1 to 3.
OBn
OBn
NaH
TeO
2) H0
Bn
Decytonpolide A R-H)
Decytospolide R- COCH)
13.25 a
13,25 d
Incorrect.
Add curved arrow(s) to draw step 1 of the mechanism for the conversion of compound 2 to compound 3 (note that the Grignard
reagent is represented as a carbanion). Modify the given drawing of the product as needed to show the intermediate that is
formed in this step.
Edit Drawing
Hint](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F445178e5-eb66-4a17-8b6f-493656b3ff53%2F36598fa5-9427-4232-92d4-1c27dac08031%2Fyl7i77j_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Decytospolides A and Bare fungal natural products that are toxic to some cancer cells, In a synthesis of these natural products.
compound 3 was prepared via the reaction between an epoxide (compound 2) and a Grignard reagent (Tetrahedron: Asymmetry 2015.
26, 296-303). Draw the structure of 2, and provide a complete mechanism for the conversion of 1 to 3.
OBn
OBn
NaH
TeO
2) H0
Bn
Decytonpolide A R-H)
Decytospolide R- COCH)
13.25 a
13,25 d
Incorrect.
Add curved arrow(s) to draw step 1 of the mechanism for the conversion of compound 2 to compound 3 (note that the Grignard
reagent is represented as a carbanion). Modify the given drawing of the product as needed to show the intermediate that is
formed in this step.
Edit Drawing
Hint
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