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Semi-pinacol strategy for constructing B-ring of pradimicin–benanomicin antibiotics

✍ Scribed by Ken Ohmori; Mitsuru Kitamura; Yuji Ishikawa; Hirohisa Kato; Mami Oorui; Keisuke Suzuki


Book ID
104251918
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
107 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


Semi-pinacol cyclization of compound 8, having an acetal and an aldehyde substituent, was achieved by employing SmI 2 and BF 3 •OEt 2 , leading to the highly stereoselective formation of cyclized product 9. The vicinal diol in 9 is discriminated, so as to allow selective glycosylation for the synthesis of pradimicin-benanomicin antibiotics.


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