Nucleophilic addition reaction of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones: synthetic approach to polyoxin C.
[reaction: see text] The stereoselectivity of nucleophilic addition of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones was investigated. It was found that the selectivity was highly dependent on the bulkiness of the C-substituent of the nitrone. The major adducts were elaborated into the key intermediate of polyoxin C.
Mita
Naka
N
Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo 204-8588, Japan.
Tamura
Osamu
O
Ishibashi
Hiroyuki
H
Sakamoto
Masanori
M
D000935:Antifungal Agents / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry*; D007202:Indicators and Reagents; D013237:Stereoisomerism
C454640:2-trimethylsilyloxyfuran; D000935:Antifungal Agents; D005663:Furans; D006574:Heterocyclic Compounds, 2-Ring; D006572:Heterocyclic Compounds, Bridged-Ring; D007202:Indicators and Reagents; C454641:polyoxin C