β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Preparation of 3-Hydroxypropyl and 4-Hydroxybutyl Propenyl Ketones from γ- and δ-Lactones. Synthesis of (±)-Rose oxide

Starting from γ‐ and δ‐lactones 1–3, a two‐step preparation of 3‐hydroxypropyl and 4‐ hydroxybutyl propenyl ketones 10–18 is described, involving as the key step the β‐cleavage of the bis(homoallylic) potassium alkoxides 4a–9a. The novel methodology is illustrated by a short synthesis of (±)‐rose ox...

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Veröffentlicht in:Helvetica chimica acta 1987-11, Vol.70 (7), p.1879-1885
Hauptverfasser: Snowden, Roger L., Linder, Simon M., Muller, Bernard L., Schulte-Elte, Karl H.
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Sprache:eng
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Zusammenfassung:Starting from γ‐ and δ‐lactones 1–3, a two‐step preparation of 3‐hydroxypropyl and 4‐ hydroxybutyl propenyl ketones 10–18 is described, involving as the key step the β‐cleavage of the bis(homoallylic) potassium alkoxides 4a–9a. The novel methodology is illustrated by a short synthesis of (±)‐rose oxide(20).
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19870700722