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

• Published in: Chemical & pharmaceutical bulletin Vol. 40; no. 2; pp. 562 - 564
• Main Authors: KONOSU, Toshiyuki, MIYAOKA, Takeo, TAJIMA, Yawara, OIDA, Sadao
• Format: Journal Article
• Language: English
• 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

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.