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

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

  • Org Lett. 2002 Apr 4;4(7):1111-4. doi: 10.1021/ol0200044.
Naka Mita 1,  Osamu Tamura,  Hiroyuki Ishibashi,  Masanori Sakamoto
Affiliations

Affiliation

  • 1 Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo 204-8588, Japan.
PMID: 11922795 DOI: 10.1021/ol0200044
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.

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