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An Alternative Access to (±)-α-Irones and (±)-β-Irone via Acid-Mediated Cyclisation

✍ Scribed by Karl H. Schulte-Elte; Hervé Pamingle; Arnold P. Uijttewaal; Roger L. Snowden

Book ID: 102258091
Publisher: John Wiley and Sons
Year: 1992
Tongue: German
Weight: 408 KB
Volume: 75
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19920750312

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✦ Synopsis

Abstract

Acid‐mediated cyclisation of trienone 8, readily available from 2,3‐dimethylbutanal (1; five steps: 47% yield), using fluorosulfonic acid (6.8 mol‐equiv.) in 2‐nitropropane at −70°, afforded a 14:9:1 mixture (70% yield) of (±)‐cis‐α‐irone (9), (±)‐trans‐α‐irone (10), and (±)‐β‐irone (11). Other acidic conditions examined, using 95% aq. H~2~SO~4~ solution, 85% aq. H~3~PO~4~ solution, or SnCl~4~, gave inferior results.

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