Synthesis of isagarin, a new type of tetracyclic naphthoquinone from Pentas longiflora

Authors
Kesteleyn, B Van Puyvelde, L De Kimpe, N
Citation
B. Kesteleyn et al., Synthesis of isagarin, a new type of tetracyclic naphthoquinone from Pentas longiflora, J ORG CHEM, 64(2), 1999, pp. 438-440
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
2
Year of publication
1999
Pages
438 - 440
Database
ISI
SICI code
0022-3263(19990122)64:2<438:SOIANT>2.0.ZU;2-H
Abstract
Isagarin (1) was synthesized in four steps from 1,4-dimethoxynaphthaldehyde (4). The key intermediate 2-(1,2-dihydroxyethyl)-1,4-naphthoquinon (3) was found to react with acylated pyridinium ylides to afford, after spontaneou s intramolecular condensation, the desired natural product isagarin (1). De pending on the type of acylated pyridinium ylides, different types of new p yranonaphthoquinone derivatives were obtained.