Stereoselective Total Synthesis of the Tricyclic Sesquiterpene (±)-Kelsoene by an Intramolecular Cu(I)-Catalyzed [2+2]-Photocycloaddition Reaction
- 25 July 2002
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2002 (8) , 1305-1307
- https://doi.org/10.1055/s-2002-32972
Abstract
The sesquiterpene kelsoene (1) has been stereoselectively prepared starting from the known 1,2,3-trisubstituted cyclopentane 7 in 14 synthetic operations. The intramolecular Cu(I)-catalyzed photocycloaddition of the precursor 10 which proceeded in 89% yield established the relative configuration of the two stereogenic centers (C-1, C-8) within the cyclobutane ring. The stereochemistry at C-6 was adjusted by the stereoselective hydrogenation of the unsaturated enone 15.Keywords
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