1. Compound 1 is an anticoagulant that is extracted from, among other plants, the sweet clover plant, Melilotus Officinalis. However, the compound is moderately toxic and also finds use as a rodenticide. Compound 1 is biosynthesised in a complex pathway starting from compounds 2 and 3 via an aldol condensation. OH OH 2 LOH + HOOC 1 3 aldol HO O OH OH 4 OH LOH (a) Provide a complete mechanism for this transformation. You do NOT need to account for the stereochemistry of the new chiral centre formed.
1. Compound 1 is an anticoagulant that is extracted from, among other plants, the sweet clover plant, Melilotus Officinalis. However, the compound is moderately toxic and also finds use as a rodenticide. Compound 1 is biosynthesised in a complex pathway starting from compounds 2 and 3 via an aldol condensation. OH OH 2 LOH + HOOC 1 3 aldol HO O OH OH 4 OH LOH (a) Provide a complete mechanism for this transformation. You do NOT need to account for the stereochemistry of the new chiral centre formed.
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:1. Compound 1 is an anticoagulant that is extracted from, among other plants, the sweet
clover plant, Melilotus Officinalis. However, the compound is moderately toxic and also
finds use as a rodenticide.
Compound 1 is biosynthesised in a complex pathway starting from compounds 2 and 3
via an aldol condensation.
OH
OH
2
OH
+
HOOC
1
3
aldol
HO
O OH OH
4
OH
LOH
(a) Provide a complete mechanism for this transformation. You do NOT need to account
for the stereochemistry of the new chiral centre formed.
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