REDUCTIVE THIOALKYLATION OF A KALAFUNGIN ANALOG

Authors
BRIMBLE MA NAIRN MR
Citation
Ma. Brimble et Mr. Nairn, REDUCTIVE THIOALKYLATION OF A KALAFUNGIN ANALOG, Tetrahedron letters, 39(27), 1998, pp. 4879-4882
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
27
Year of publication
1998
Pages
4879 - 4882
Database
ISI
SICI code
0040-4039(1998)39:27<4879:RTOAKA>2.0.ZU;2-T
Abstract
Reduction of pyranonaphthoquinone 3 with sodium dithionite in the pres ence of the sulfur nucleophiles thiocresol, benzylmercaptan and butane thiol afforded the thioalkylated products 4,5; 6,7; and 8,9 respective ly. The isolation of these products provides the first example of the ability of pyranonaphthoquinone antibiotics such as kalafungin 1 to un dergo reductive thioalkylation at the C-4 position. (C) 1998 Elsevier Science Ltd. All rights reserved.