Norrish Type I Cleavage of 9-Oxabicyclo[3.3.1]nonan-3-one : A Straightforward Synthesis of (±)-(cis-6-Methyletrahydropyran-2-yl)acetic Acid, a Constituent of Civet

• Published in: Chemical & pharmaceutical bulletin Vol. 43; no. 3; pp. 517 - 519
• Main Authors: OKUMURA, Masafumi, MURAOKA, Osamu, MAEDA, Tomomi, TANABE, Genzoh, WANG, Lichen
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 1995; 公益社団法人日本薬学会; Pharmaceutical Soc Japan
• Subjects: (cis-methyltetrahydropyran-2-yl)acetic acid; 9-oxabicyclo[3.3.1]nonan-3-one; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; civet; Life Sciences & Biomedicine; Norrish type I reaction; Pharmacology & Pharmacy; photo-reaction; photo-reduction; Physical Sciences; Science & Technology; ROUTE; PHOTO-REACTION; SPECTROSCOPY; (CIS-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID; PHOTO-REDUCTION; 9-OXABICYCLO[3.3.1]NONAN-3-ONE; CONFORMATIONAL-ANALYSIS; CIVET; NORRISH TYPE I REACTION; DERIVATIVES; 9-AZABICYCLO<3.3.1>NONAN-3-ONE
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.43.517

The photo-reaction of 9-oxabicyclo[3.3.1]nonan-3-one (2) was investigated. Upon irradiation in methanol, the ketone (2) predominantly gave the methanol adduct, 3-hydroxymethyl-9-oxabicyclo[3.3.1]nonan-3-ol (3), accompanied with photo-reduced products, exo- and endo-9-oxabicyclo[3.3.1]nonan-3-ol (4 and 5). Irradiation in water resulted in Norrish type I cleavage to give directly (cis-6-methyletrahydropyran-2-yl)acetic acid (1), a constituent of civet, in moderate yield.