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Communication | Special issue | Vol 13, No. 1, 1979, pp.191-196
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0191
Transformation of α-Dihydroionol to Dihydroedulan and Theaspyrane by Photosensitized Oxygenation

Hideki Okawara, Susumu Kobayashi, and Masaji Ohno*

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


Racemic dihydroedulan (1) and theaspyrane (2) have been synthesized starting with racemic α-dihydroionol (3) in a few steps using photosensitized oxygenation as the key step. Two isomeric hydroxy allyl alcohols 4 and 5 were obtained upon treatment with singlet oxygen and also prepared from an epoxide 7 by treatment with lithium diethylamide and organoselenium reagents, respectively. The allyl alcohol 5 afforded dihydroedulan (1) predominantly with BF3 in THF and another allyl alcohol 4 was converted selectively to theaspyrane (2) through a diene 9.