Organic Letters 2002-04-04

Nucleophilic addition reaction of 2-trimethylsilyloxyfuran to N-gulosyl-C-alkoxymethylnitrones: synthetic approach to polyoxin C.

Naka Mita, Osamu Tamura, Hiroyuki Ishibashi, Masanori Sakamoto

Index: Org. Lett. 4 , 1111, (2002)

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Abstract

[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.