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 | Zendy

Snowden Roger L. | Zendy; Linder Simon M. | Zendy; Muller Bernard L. | Zendy; SchulteElte Karl H. | Zendy

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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

Author(s) -

Snowden Roger L.,

Linder Simon M.,

Muller Bernard L.,

SchulteElte Karl H.

Publication year - 1987

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19870700722

Subject(s) - chemistry , propenyl , cleavage (geology) , potassium , oxide , medicinal chemistry , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering

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 ).

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