Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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A key step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involved the reaction of compound A and dihalide B with two equivalents of LDA to form C. Draw a stepwise mechanism for this reaction. β-Vetivone contains a spiro ring system—that is, two rings that share a single carbon atom.
Heating A results in two successive [3,3] sigmatropic rearrangements–Claisen reaction followed by Cope reaction–to afford β-sinensal, a component of mandarin orange oil. What is the structure of β-sinensal?
A key step in the synthesis of the antidepressant paroxetine (trade name Paxil) involves a Williamson ether synthesis of the acyclic ether in X. Draw two different routes to this ether and state which is preferred.
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