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researchers developed the total synthesis of (-)-strictosidine, a biosynthetic precursor to a wide variety of naturally occurring complex molecules NH H HO OH H OH OH MeO₂C (-)-Strictosidine One key step in the reported synthesis of (-)-strictosidine involves the following Diels-Alder reaction between the shown two fragments. The dienophile is the large complex with the 6- membered hexose ring, and the diene is the 5-membered ring compound with two carbonyl groups. This reaction ultimately produces a heterocycle, or a cyclic compound that has a non-carbon atom in the ring. TBSO AcO- OAC OAC OAC ? 50°C hexafluoroisopropanol (solvent) diene * ACO = dienophile TBSO = a) The diene has three unsaturated groups - one alkene and two carbonyls. Using the symbols below, indicate the two out of the three unsaturated groups that will form the "diene" that participates in the Diels-Alder reaction. Please explain briefly. B A b) The diene and dienophile can be reacted together to form two potential products of the Diels-Alder reaction. These two products are constitutional isomers of one another, where one product can be formed by flipping the dienophile in the other. Please predict the major product and justify your answer using resonance structures. Do not indicate stereochemistry. You may use the following abbreviation as shorthand in the dienophile: AcO OAc OAC OAC = OTHP

researchers developed the total synthesis of (-)-strictosidine, a biosynthetic precursor to a wide variety of naturally occurring complex molecules NH H HO OH H OH OH MeO₂C (-)-Strictosidine One key step in the reported synthesis of (-)-strictosidine involves the following Diels-Alder reaction between the shown two fragments. The dienophile is the large complex with the 6- membered hexose ring, and the diene is the 5-membered ring compound with two carbonyl groups. This reaction ultimately produces a heterocycle, or a cyclic compound that has a non-carbon atom in the ring. TBSO AcO- OAC OAC OAC ? 50°C hexafluoroisopropanol (solvent) diene * ACO = dienophile TBSO = a) The diene has three unsaturated groups - one alkene and two carbonyls. Using the symbols below, indicate the two out of the three unsaturated groups that will form the "diene" that participates in the Diels-Alder reaction. Please explain briefly. B A b) The diene and dienophile can be reacted together to form two potential products of the Diels-Alder reaction. These two products are constitutional isomers of one another, where one product can be formed by flipping the dienophile in the other. Please predict the major product and justify your answer using resonance structures. Do not indicate stereochemistry. You may use the following abbreviation as shorthand in the dienophile: AcO OAc OAC OAC = OTHP

Organic Chemistry
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 24.37P
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part a and b please

researchers developed the total synthesis of (-)-strictosidine, a biosynthetic precursor to a wide variety of naturally occurring complex molecules NH H HO OH H OH OH MeO₂C (-)-Strictosidine One key step in the reported synthesis of (-)-strictosidine involves the following Diels-Alder reaction between the shown two fragments. The dienophile is the large complex with the 6- membered hexose ring, and the diene is the 5-membered ring compound with two carbonyl groups. This reaction ultimately produces a heterocycle, or a cyclic compound that has a non-carbon atom in the ring. TBSO AcO- OAC OAC OAC ? 50°C hexafluoroisopropanol (solvent) diene * ACO = dienophile TBSO = a) The diene has three unsaturated groups - one alkene and two carbonyls. Using the symbols below, indicate the two out of the three unsaturated groups that will form the "diene" that participates in the Diels-Alder reaction. Please explain briefly. B A b) The diene and dienophile can be reacted together to form two potential products of the Diels-Alder reaction. These two products are constitutional isomers of one another, where one product can be formed by flipping the dienophile in the other. Please predict the major product and justify your answer using resonance structures. Do not indicate stereochemistry. You may use the following abbreviation as shorthand in the dienophile: AcO OAc OAC OAC = OTHP
Transcribed Image Text:researchers developed the total synthesis of (-)-strictosidine, a biosynthetic precursor to a wide variety of naturally occurring complex molecules NH H HO OH H OH OH MeO₂C (-)-Strictosidine One key step in the reported synthesis of (-)-strictosidine involves the following Diels-Alder reaction between the shown two fragments. The dienophile is the large complex with the 6- membered hexose ring, and the diene is the 5-membered ring compound with two carbonyl groups. This reaction ultimately produces a heterocycle, or a cyclic compound that has a non-carbon atom in the ring. TBSO AcO- OAC OAC OAC ? 50°C hexafluoroisopropanol (solvent) diene * ACO = dienophile TBSO = a) The diene has three unsaturated groups - one alkene and two carbonyls. Using the symbols below, indicate the two out of the three unsaturated groups that will form the "diene" that participates in the Diels-Alder reaction. Please explain briefly. B A b) The diene and dienophile can be reacted together to form two potential products of the Diels-Alder reaction. These two products are constitutional isomers of one another, where one product can be formed by flipping the dienophile in the other. Please predict the major product and justify your answer using resonance structures. Do not indicate stereochemistry. You may use the following abbreviation as shorthand in the dienophile: AcO OAc OAC OAC = OTHP
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