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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 ).