Question
Answer the following about the Wieland-Miescher ketone and its use in total synthesis, for 10 points each.
[10h] This chemist’s total synthesis of Taxol uses a single enantiomer of the Wieland-Miescher ketone as a starting material. A butadiene derivative named after this chemist exhibits unusual reactivity in Diels-Alder reactions.
ANSWER: Samuel J. Danishefsky [accept Danishefsky’s diene or Danishefsky Taxol total synthesis]
[10m] In their work on total syntheses, Hajos (“HOY-yosh”) and Parrish recorded the synthesis of the Wieland-Miescher ketone via this reaction. This two-step reaction consists of a Michael addition followed by an aldol condensation.
ANSWER: Robinson annulation
[10e] The AB-ring structure of the Wieland-Miescher ketone makes it an attractive starting material for the synthesis of this class of compounds, which are characterized by four fused rings and include estradiol and testosterone.
ANSWER: steroids [accept steroid hormones]
<Science - Chemistry>
Summary
| 2024 ARGOS @ Brandeis | 03/22/2025 | Y | 3 | 16.67 | 100% | 33% | 33% |
| 2024 ARGOS @ Chicago | 11/23/2024 | Y | 6 | 16.67 | 67% | 50% | 50% |
| 2024 ARGOS @ Christ's College | 12/14/2024 | Y | 3 | 10.00 | 100% | 0% | 0% |
| 2024 ARGOS @ Columbia | 11/23/2024 | Y | 3 | 10.00 | 67% | 33% | 0% |
| 2024 ARGOS @ McMaster | 11/17/2024 | Y | 5 | 18.00 | 100% | 60% | 20% |
| 2024 ARGOS @ Stanford | 02/22/2025 | Y | 3 | 23.33 | 100% | 100% | 33% |
| 2024 ARGOS Online | 03/22/2025 | Y | 3 | 16.67 | 67% | 67% | 33% |
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