Inthomycin C, a natural product produced by Streptomyces bacteria, is known to inhibit the production of cellulose, an important component of the cell wall of plants. A recent synthesis of inthomycin C involved a thermal electrocyclic ring-opening reaction, as outlined below. (Org. Lett. 2013, 15, 3242-3245.) There are two products that are possible under thermal conditions, but only one of these products was observed. Identify the product and explain why the other product was not observed. CO₂H ? → Br 16.22a H Heat E Identify the two products that are possible under thermal conditions. (Select all that apply.) Br CO₂H Br CO₂H W P X Inthomycin C E OH hulu NH₂ 12:20 AM 7/13/2023

Inthomycin C, a natural product produced by Streptomyces bacteria, is known to inhibit the production of cellulose, an important component of the cell wall of plants. A recent synthesis of inthomycin C involved a thermal electrocyclic ring-opening reaction, as outlined below. (Org. Lett. 2013, 15, 3242-3245.) There are two products that are possible under thermal conditions, but only one of these products was observed. Identify the product and explain why the other product was not observed. CO₂H ? → Br 16.22a H Heat E Identify the two products that are possible under thermal conditions. (Select all that apply.) Br CO₂H Br CO₂H W P X Inthomycin C E OH hulu NH₂ 12:20 AM 7/13/2023

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 33MP

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