e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

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

Full Text: HTML

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 ...

1-(1-hydroxy-3-butenyl)-2-isopropenylcyclopentene Structure

1-(1-hydroxy-3-...

~94%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

~%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

~%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

~%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

2-isopropenylcyclopentene-1-carbaldehyde Structure

2-isopropenylcy...

~%

1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

1-(2-prop-1-en-...

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

~%

2-phenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-phenyl-1-(2-p...

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

~%

2-phenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-phenyl-1-(2-p...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

~%

2-phenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-phenyl-1-(2-p...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

2-phenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-phenyl-1-(2-p...

2-isopropenylcyclopentene-1-carbaldehyde Structure

2-isopropenylcy...

~%

2-phenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-phenyl-1-(2-p...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

isopropenylboronic acid pinacol ester Structure

isopropenylboro...

~89%

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

~82%

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

~%

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

1-(2-isopropenyl-cyclopent-1-enyl)-2-vinyl-but-3-en-1-ol Structure

1-(2-isopropeny...

~50%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

~%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

~%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

~%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

2-isopropenylcyclopentene-1-carbaldehyde Structure

2-isopropenylcy...

~%

2-ethenyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-ethenyl-1-(2-...

(2-prop-1-en-2-ylcyclopenten-1-yl)methanol Structure

(2-prop-1-en-2-...

~%

2-methyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-methyl-1-(2-p...

ethyl 2-prop-1-en-2-ylcyclopentene-1-carboxylate Structure

ethyl 2-prop-1-...

~%

2-methyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-methyl-1-(2-p...

Ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-1-ene-1-carboxylate Structure

Ethyl 2-{[(trif...

~%

2-methyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-methyl-1-(2-p...

Ethyl 2-oxocyclopentanecarboxylate Structure

Ethyl 2-oxocycl...

~%

2-methyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-methyl-1-(2-p...

2-isopropenylcyclopentene-1-carbaldehyde Structure

2-isopropenylcy...

~%

2-methyl-1-(2-prop-1-en-2-ylcyclopenten-1-yl)but-3-en-1-one Structure

2-methyl-1-(2-p...