PROTECTING GROUP IMPROVEMENT BY ISOTOPIC-SUBSTITUTION - SYNTHESIS OF THE QUINONE SYSTEM OF FREDERICAMYCIN-A

Authors
CLIVE DLJ CANTIN M KHODABOCUS A KONG XL TAO Y
Citation
Dlj. Clive et al., PROTECTING GROUP IMPROVEMENT BY ISOTOPIC-SUBSTITUTION - SYNTHESIS OF THE QUINONE SYSTEM OF FREDERICAMYCIN-A, Tetrahedron, 49(36), 1993, pp. 7917-7930
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
36
Year of publication
1993
Pages
7917 - 7930
Database
ISI
SICI code
0040-4020(1993)49:36<7917:PGIBI->2.0.ZU;2-X
Abstract
Use of a trideuteriomethyl group for protection of phenolic oxygen (as in 29, Scheme 4), instead of the classical methyl group, serves to su ppress an unwanted intramolecular hydrogen transfer (12-->14, Scheme 2 ) during radical cyclization. The resulting spiro compound (31, Scheme 5) can be converted, by selective demethylation and oxidation, into a substance (35, Scheme 6) that represents the spirodiketone-quinone sy stem of the antitumor agent Fredericamycin A.