Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Draw a stepwise mechanism for the following reaction, a key step in the synthesis of vernakalant, a drug approved in Europe in 2010 for the treatment of atrial fibrillation. Pure B was separated from a mixture of diastereomers. Your mechanism must explain the trans stereochemistry of the two substituents on the six-membered ring.
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?
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