Synthesis of (-)-gloeosporone, a fungal autoinhibitor of spore germination using a pi-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction.
The synthesis of the germination self-inhibitor (-)-Gloeosporone is reported. The embedded 1,7-diol motif in the product is constructed by an ironcarbonyl tether controlled Mukaiyama aldol reaction. The key step in the synthesis is the reductive removal of the ligating iron species by treatment of an acetoxycomplex 6 with lithium naphthalenide.
Ley
Steven V
SV
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW. svl1000@cam.ac.uk
Cleator
Ed
E
Harter
Jürgen
J
Hollowood
Christopher J
CJ
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020231:Colletotrichum / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D013172:Spores, Fungal / Q000187:drug effects* / Q000502:physiology
D000935:Antifungal Agents; D007783:Lactones; C484172:gloeosporone