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Detours en route to a total synthesis of (+)-cassiol

✍ Scribed by Marı́a I. Colombo; Juan Zinczuk; Marı́a L. Bohn; Edmundo A. Rúveda

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
279 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described.

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