SYNTHESIS OF ANGUCYCLINES .8. BIOMIMETIC-TYPE SYNTHESIS OF RABELOMYCIN, TETRANGOMYCIN, AND RELATED RING-B AROMATIC ANGUCYCLINONES

Authors
KROHN K BOKER N FLORKE U FREUND C
Citation
K. Krohn et al., SYNTHESIS OF ANGUCYCLINES .8. BIOMIMETIC-TYPE SYNTHESIS OF RABELOMYCIN, TETRANGOMYCIN, AND RELATED RING-B AROMATIC ANGUCYCLINONES, Journal of organic chemistry, 62(8), 1997, pp. 2350-2356
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
8
Year of publication
1997
Pages
2350 - 2356
Database
ISI
SICI code
0022-3263(1997)62:8<2350:SOA.BS>2.0.ZU;2-J
Abstract
The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared-i n a biomimetic-type synthesis by two successive aldol cyclizations sta rting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions, The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the ph enolic anthraquinones 16a-c upon treatment with excess NMO.