Total synthesis of angucyclines. Part 13: Biomimetic-type approach to a potential precursor of the landomycinone angucyclinone

Authors
Krohn, K Frese, P Freund, C
Citation
K. Krohn et al., Total synthesis of angucyclines. Part 13: Biomimetic-type approach to a potential precursor of the landomycinone angucyclinone, TETRAHEDRON, 56(9), 2000, pp. 1193-1196
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
9
Year of publication
2000
Pages
1193 - 1196
Database
ISI
SICI code
0040-4020(20000225)56:9<1193:TSOAP1>2.0.ZU;2-6
Abstract
The dimethoxy naphthalene derivative 10 with two vicinal side chains was pr epared by reaction of the dibromide 7 with silyl ether 8 ([Bu4N][Ph3SnF2]-c atalysis) followed by Stille reaction of 9 with stannane 5. Acidic hydrolys is gave the triketo ester 11 that cyclized in a biomimetic-type reaction to the highly substituted dihydro benz[a]anthracene 12, a potential precursor of the angucyclinone landomycinone. (C) 2000 Elsevier Science Ltd. All rig hts reserved.