Synthesis of pyran and pyranone natural products.
An overview of the synthesis of the fungal metabolites (+)-dermolactone, (-)- semixanthomegnin, (+)- and (-)-mellein, (-)-ochratoxin alpha, (-)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as (3S,3'S)-xylindein is also outlined.
Donner
Christopher D
CD
School of Chemistry, The University of Melbourne, Parkville, Victoria 3010, Australia.
Gill
Melvyn
M
Tewierik
Leonie M
LM
D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry; D005658:Fungi / Q000737:chemistry / Q000378:metabolism; D049934:Isocoumarins / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D009793:Ochratoxins / Q000138:chemical synthesis / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D016227:Benzoquinones; D049934:Isocoumarins; D009285:Naphthoquinones; D009793:Ochratoxins; D010636:Phenols; D011083:Polycyclic Compounds; D011714:Pyrans; D011753:Pyrones; C501541:ventiloquinone L; C419334:xylindein; C000426:5-chloro-8-hydroxy-3,4-dihydro-3-methylisocoumarin-7-carboxylic acid; C004532:quinone; C120538:ochracin