Tetrahedron letters

Investigations towards the synthesis of (−)-coprinolone, via a thermal 8π–6π electrocyclization cascade of 1, 5, 7-trien-4-ones

…, HA Wegner, MF Jacobsen, RM Adlington, JE Baldwin

Index: Lawrence, Andrew L.; Wegner, Hermann A.; Jacobsen, Mikkel F.; Adlington, Robert M.; Baldwin, Jack E. Tetrahedron Letters, 2006 , vol. 47, # 49 p. 8717 - 8720

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Citation Number: 7

Abstract

(−)-Coprinolone 1 is an unusual oxygen-bridged protoilludane sesquiterpene ketol, isolated from the fungus Coprinus psychromorbidus, which has been the subject of many studies due to the extensive damage it causes to overwintering cereals, grasses and legumes in western Canada. 1 and 2 The unusual tricyclic ether bridged structure of (−)-coprinolone 1 with its seven chiral centres, two of which are quaternary, makes it an attractive target for synthetic ...