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)

Full Text: HTML

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.

Related Compounds

  • 2-trimethylsilylox...

Related Articles:

Simple diastereoselectivity of the BF3.OEt2-catalyzed vinylogous Mukaiyama aldol reaction of 2-(trimethylsiloxy)furans with aldehydes.

2005-04-29

[J. Org. Chem. 70(9) , 3654-9, (2005)]

G. Desimoni et al.

[Tetrahedron 57 , 10203, (2001)]

G. Casiraghi et al.

[J. Org. Chem. 55 , 2565, (1990)]

G. Rassu et al.

[Tetrahedron 49 , 6627, (1993)]

M.A. Brimble et al.

[Tetrahedron Lett. 29 , 5987, (1988)]

More Articles...