Pigments of fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid

Authors
Gill, M Harte, MF Ten, A
Citation
M. Gill et al., Pigments of fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid, AUST J CHEM, 53(4), 2000, pp. 245-256
Citations number
38
Categorie Soggetti
Chemistry
Journal title
AUSTRALIAN JOURNAL OF CHEMISTRY
ISSN journal
00049425 → ACNP
Volume
53
Issue
4
Year of publication
2000
Pages
245 - 256
Database
ISI
SICI code
0004-9425(2000)53:4<245:POFL-S>2.0.ZU;2-6
Abstract
The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein ( 1) is synthesized for the first time in enantiomerically pure form by Diels -Alder cycloaddition between the functionalized butadiene derivative (8) an d the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the l atter being derived from (R)-citramalic acid (3). The natural products (1S, 3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepar ed for the first time by using the same strategy.