PAYNE REARRANGEMENT ROUTE TO THE OPTICALLY ACTIVE OXIRANE PRECURSOR FOR THE PREPARATION OF TRIAZOLE ANTIFUNGALS

Optically active epoxide 1, an important intermediate for the preparation of antifungal triazole-amides 2, was synthesized starting from the (S)-lactic acid- derived ketone 9 and taking advantage of the Payne rearrangement of the epoxyalocohol 8.

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 40; no. 2; pp. 562 - 564
Main Authors KONOSU, Toshiyuki, MIYAOKA, Takeo, TAJIMA, Yawara, OIDA, Sadao
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1992
Pharmaceutical Soc Japan
Maruzen
Subjects
(S)-lactic acid
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Life Sciences & Biomedicine
Organic chemistry
oxirane
Payne rearrangement
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
stereocontrol
triazole antifungal
PAYNE REARRANGEMENT
(S)-LACTIC ACID
STEREOCONTROL
TRIAZOLE ANTIFUNGAL
OXIRANE
Stereoselectivity
Epoxidation
Chemical rearrangement
Five membered ring
Fluorine Organic compounds
Nitrogen heterocycle
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Summary:Optically active epoxide 1, an important intermediate for the preparation of antifungal triazole-amides 2, was synthesized starting from the (S)-lactic acid- derived ketone 9 and taking advantage of the Payne rearrangement of the epoxyalocohol 8.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.40.562