Irradiation of hydroxyalkyl glucosides in the presence of mercury(II) oxide and iodine gave glucosidic C-1-spiroorthoesters. Where the starting glycoside had CH2OH, the cyclization was regio- and stereo-specific by .alpha.-attack. The C-1-spiroorthoesters were readily available in a 1-pot synthesis starting from glucosyl halides. [Spiroorthoesters are found in some antibiotics].
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN
TAMARU, M
HORITO, S
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN
HORITO, S
YOSHIMURA, J
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN
TAMARU, M
HORITO, S
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN
HORITO, S
YOSHIMURA, J
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TOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPANTOKYO INST TECHNOL, FAC SCI, CHEM NAT PROD LAB, MIDORI KU, YOKOHAMA, KANAGAWA 227, JAPAN