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Formal Synthesis of Galantinic Acid by Oxo-Diels–Alder Methodology

✍ Scribed by Wojciech Chaładaj; Janusz Jurczak

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
488 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

This communication presents a simple and efficient enantioselective route to galantinic acid. The strategy is based on a highly enantioselective hetero‐Diels–Alder (HDA) reaction of 3‐(4‐methoxybenzyloxy)propanal with Danishefsky's diene followed by selective introduction of further stereogenic centers thanks to the rigidity of the dihydropyran ring. The key HDA reaction is catalyzed by a new salen Cr^III^ complex bearing a 1,1‐diphenylethyl substituent at the 3‐position of the salicyliden moiety.

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