title: A convenient 3-step synthesis of (R)-7-hydroxycarvone from (S)-alpha-pinene.
abstract: A convenient 3-step synthesis of (R)-7-hydroxycarvone (2) has been developed starting from (S)-alpha-pinene (7), using photooxygenation, oxidation, and fragmentation reactions. An improved synthesis of epoxy alcohol 6 and an unusual Ti(OiPr)(4) catalyzed hydroxy epoxide to keto alcohol rearrangement are also described.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA.
authors.forename: Rajamma
authors.initials: R
authors.lastname: Lakshmi
authors.forename: T David
authors.initials: TD
authors.lastname: Bateman
authors.forename: Matthias C
authors.initials: MC
authors.lastname: McIntosh
mesh_terms: D000081008:Bicyclic Monoterpenes; D002384:Catalysis; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: C502155:(R)-7-hydroxycarvone; D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; C005451:alpha-pinene